8 mins to read

The dating diary of a serial entrepreneur

Book Review: A Kiwi businesswoman's search for the perfect partner.

Nevil Gibson Sun, 18 Jul 2021

In a recent rant, British journalist Ella Whelan took aim at Mary Ann Sieghart’s feminist tract The Authority Gap for stoking “grievances of a small section of women (and obsequious men) who believe politics should revolve around such radical calls as gender quotas for big business.”

Whelan describes the book as an exercise in an elitism of “insufferable snobbery” that is blocking progress in all women’s freedom. She accuses Seighart of all but ignoring issues, such as childcare and upping the pay of working women, in favour of corporate feminism, while fatuously complaining that rich and successful women are still not given the respect they deserve from their peers.

Obviously, there’s more than one path for women to be successful and achieve their ambitions. Rebekah Campbell is one who’s taken the time to tell her story in the most personal way.

Scottish-born, she was three when her parents emigrated to New Zealand. They eventually settled in Wellington, where Rebekah attended Wellington Girls’ College and Victoria University.

As a student of politics and the Maori language, she became alarmed in the high rate of youth suicide. Her entrepreneurial streak and interest in music combined to create the Levi’s Life Festival, a pop concert that attracted 15,000 and raised $100,000 for the cause.

Two years later, at 21, she moved to Sydney for a nine-year career in the music industry, managing pop bands and establishing a recording company, Scorpio Music. It had a website promoting concerts that rewarded ticket-buyers who passed on recommendations to other fans.

It was an idea that led to a startup,, an app that widened the business scope to retailers and suppliers such as restaurants, bars, gyms and hairdressers. The concept caught on and had a revenue stream from the get-go, as retailers paid a monthly fee to join the reward scheme. 

Referrals by users earned points that were converted into free or discounted goods and services. Retailers benefited because they could sell deals to a regular base of customers rather than rely on one-off promotions from other deal sites. 

Rebekah Campbell

Keenly sought
Campbell became an established identity on the Sydney IT scene and was keenly sought after on the speaking circuit with her experiences in raising capital, running a business, managing a team and being accountable to a board of directors. A promotional interview in New York resulted in her blog becoming a source for a New York Times column, You’re the Boss, that raised her profile even higher.

None of this came without effort and sacrifice, but her largest fear at 33 was being unmarried and that she might miss out on having a family. Like many of her male equivalents, Campbell admits her single-minded dedication to business pushed her private life into the background. 

While on a solitary holiday in Bali, she decided to change course and go into the dating game. Campbell had never had a serious relationship since her university days. It lasted a couple of years before they drifted apart. Sadly, the boyfriend died in a car accident in 2001 aged 24, ending any possibility of a reconnection.  

Learning the ropes
From her base in Sydney’s Darlinghurst, Campbell started to learn the ropes from a local version of Tinder. Her modus operandi included at least one date a week, and a preliminary phone conversation to test compatibility and credentials. 

That was followed by a cocktail hour drink at a regular bar she trusted. This required making sure the staff didn’t treat her as a “regular.” If the guy checked a few boxes for acceptability, a follow-up date might ensue. Otherwise, an honest phone call would end anything before it started.

After the first date, which went better than expected, Campbell drew up some rules that reflected her business-like approach. Summarised, they emphasised directness and honesty in deciding on whether to continue or to break off the possibilities of romance.

Her main conclusions were not to waste anyone’s time by pursuing a relationship that did not reach her high expectations; end a relationship with a conversation, not a text; and give honest reasons rather than make up false excuses.

After learning this much from her first date, Campbell adds to her repertoire of advice from subsequent encounters with a remarkable variety of masculine behaviour that ranges from the truly awful to those that are close to perfect. Men could learn a lot from these chapters.

Venture capital
Meanwhile, Campbell’s business life continued, taking her to Silicon Valley for a round of meetings with venture capitalists, who failed to impress. 

“Almost every appointment is the same: a wooden building with glass doors, a receptionist who offers bottled water and directs me to a meeting room,” she recalls. “The venture capitalist (VC) arrives: male, mid-thirties, Ivy League haircut, pastel shirt tucked in, cotton pants and boat shoes. We shake hands, I whip out my laptop and start the presentation.

“He smiles with white teeth, says how much he's always wanted to visit Australia, takes notes, makes positive noises and promises to be in touch.”

In three days she does this 16 times, noting no women are present and, like her dating so far, that nothing seems to click. The parallels between the two are telling: “There’s a face-to-face meeting, a game of question and answer, and then a request. Will you give me a million dollars? Will you go out with me?”

But her efforts aren’t in vain. A chance invitation to a corporate knees-up in Hawaii leads to some contacts who find, a promising prospect, substantial capital is raised, the New York Times commissions a column, and speaking engagements flood in.

Rebekah Campbell with family

The dating continues 
At 36, with 78 dates completed, Campbell is starting to panic about her fertility ticking clock. She even takes medical advice on whether to freeze some of her eggs. Still, nothing seems to work. 

One date with an eligible and high-profile politician lasts for six weeks; a time she is advised that it is okay to have sex. Both are reluctant to rush it. Campbell says she still carries the baggage of her first boyfriend and regrets she let him go.

She decides the timing is right but the politician turns up late without a gift or flowers. Bad sign. She follows through but the next morning he’s off for a breakfast meeting. When he next calls, the phone has been accidentally speed-dialled. All she hears is the background noise of a meeting.

Seriously wealthy, would-be investors pose different dilemmas. One shouts a weekend in the Hamptons and a US$400 meal at a fancy restaurant. What does he want in return? Nothing, it turns out.

Another who is visiting Sydney starts dinner with an $890 bottle of Bollinger, following it with caviar, oysters and lobster. The bill reaches $1800 and he wants to address the “elephant in the room.” She doesn’t see or buy it.

Happy ending
The body clock keeps ticking and in 2014 Campbell turns 37 – egg freezing time and date 109. She thinks of quitting altogether; her appearance, dieting and dating. But she pushes on, “a blur of faces, ‘getting to know you’ stories and awkward goodbyes.”  

It ends the next year with Date 138, the title of Campbell’s own version of Bridget Jones’s Diary, and the arrival of Rod, an education lecturer, Mr Right, the perfect man.

The timing coincides with Westpac making an investment in Posse through a merger with another startup, Beat the Q, and the bank’s Hey You app. Westpac’s then New Zealand boss, David McLean, makes a late appearance at the critical board meeting, one of many named real people that pop up. However, others names have been changed or created, for obvious reasons. 

The story stops at Christmas 2020, with Rebekah, Rod and their two children at her parents’ home in Wellington, where they all now live.

Campbell has packed a lot of life’s learning in her 40 years, from the selection of a partner to the coalface of business. After reading her story, many will agree it’s one they could find valuable as well.  

138 Dates: The true story of one woman’s search for everything, by Rebekah Campbell (Allen & Unwin)

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The dating diary of a serial entrepreneur