How a Hollywood star, marriage equality and tragedy shaped venture capitalist Rachael Neumann
Flying Fox Ventures co-founder Rachael Neumann isn’t afraid of business failure because the venture capitalist has learnt you can’t control everything.
Rachael Neumann and Jodie Auster took their first born on his first long-haul flight when he was just six weeks old in April 2011.
“We went to America to introduce Miles to my family,” says Neumann, a management consultant-turned-venture capitalist who hails from Long Island, New York, but has lived in Melbourne since 2009.
“Most normal, sane parents would not have travelled with a six week old back to New York.”
It is a trip now forever burned in her memory. It was the last time she hugged her younger brother, Jacob.
“That was the only time that my brother ever met Miles. I have this beautiful picture of him holding him. I feel really grateful that at least that happened,” she says.
On September 28, 2021, Jacob Neumann was killed in a motorcycle accident in Arizona. He was only 21. The day before Jacob died, he Skyped with Miles and his sister for 40 minutes, exclaiming how much he “absolutely-freakin-lutely” adored his nephew.
“It was really something that was not even on my radar as a possibility,” Neumann now says of his passing.
“It hits you losing a sibling. Then in this moment of early motherhood, you think about what it might be like to lose a child. I joke I’ve only been to therapy with my wife twice in our in our 15-year relationship.
“One was to deal with her lateness. The other one was to work through the fact that I didn’t want to have a second child.
“I thought the more kids I had, the more risk of something happening to them. So I actually had to work through that. I’m glad I did, because I now have a beautiful daughter.” Juliet was born in 2015.
Neumann and Auster were married in America in August 2013, two months after the US Supreme Court formerly recognised marriage equality.
“We went to City Hall in the morning to get married and to the courthouse in the afternoon to finalise my son’s adoption. We just thought, ‘Let’s tick every box there is to tick’,” Neumann says.
Nearly a decade on, Miles is almost a teenager, Juliet is eight and Neumann and Auster have carved their own paths in the Australian technology and corporate sectors.
Neumann is the co-founder of Flying Fox Ventures, a rapidly expanding early stage venture capital firm. She is also a former managing director of event management tech platform Eventbrite Australia and now on the Council of Trustees for the National Gallery of Victoria, fulfilling her long-held passion for art.
Auster is a strategic adviser to the global chief executive at ride-share giant Uber after previously running its food delivery subsidiary, Uber Eats, in the Asia Pacific.
In July she started a three-year term as a director of Australia Post and is on the board of listed investment company AMCIL.
Neumann also has another, less-known claim to fame: She is one of the best friends and an ex-school buddy of Academy Award-winning actor Natalie Portman.
They have just spent a month together while Portman was visiting Australia and New Zealand for the women’s soccer World Cup. Neumann is also an investor in Los Angeles’ Angel City Football Club – the US soccer team Portman founded in 2020.
“It is always the best to spend time with her. I’ve been papped by photographers at many things with her and I’m slightly offended I am not identified as her new love interest,” Neumann quips with a smile.
She believes that dealing with the grief following her brother’s passing was a profound turning point in her life. Initially, she threw herself into her work. But then she recalls standing in a coffee queue a few months after his death.
“I remember thinking, ‘No one here knows that my brother just died and this pain that I’m feeling’. It made me realise that you literally have no idea what’s going on in people’s lives,” she says.
“Everyone is fighting their own battles. So that was one kind of insight that I try and take through my life.”
It has also shaped her work with thousands of start-ups around the globe, including as head of start-ups for Amazon Web Services in Australia and New Zealand, and now at Flying Fox.
The latter firm has already deployed $25m in funding into 50 companies and is raising at least $20m for a more traditional fixed-term fund that will make 30 to 40 investments in early stage start-ups.
One of its backers is Rachael’s friend and mentor, Reserve Bank of Australia director Carol Schwartz and her husband Alan.
“I think living in this world of start-ups where anything can happen, where all of a sudden you get a pandemic or the sentiment around the industry changes overnight, you can’t control those things,” Neumann says.
“You just manage through it with as steady a hand as possible. So I think that’s actually what my brother’s death taught me is everyone is fighting a battle that’s invisible to you and there is no rhyme or reason. You have control over very, very little.”
Rising from adversity
Neumann’s father’s parents were Holocaust survivors who escaped from Vienna and Berlin to settle in New York. German was never spoken in their home. They would never buy a German car and deliberately gave all of their children Anglo-sounding names.
Her mother was one of eight children born into a Lutheran Church-going family outside of Buffalo, New York, who had never met a Jewish person until she met Neumann’s father, Peter.
After leaving school, Neumann completed an undergraduate degree at Stanford University and two Masters degrees from Columbia University.
Her stint at Stanford came after she scored a scholarship there to play soccer and lacrosse. She played goalkeeper in both sports. Her mental coach at Stanford was famed sports psychologist Dr Jerry Lynch.
“This was very early in the days of the mental game as being important as your physical. We did visualisation on ‘How do I fail and how do I reset?’. My coach would have me mentally play the game 10 to 20 times more than I played it on the field,” Neumann says.
“Those skills are things I bring forward in my life. I always ask ‘What is the worst case scenario here?’ Once you have identified it, play it over 100 times in your mind and you are ready to deal with it if it happens.”
She still has two mental coaches – one in America and one in Australia.
Neumann believes her experience of elite sport has taught her to challenge what she calls the “hustle culture” of the modern world that she believes is detrimental to financial returns in business.
“Elite athletes always work recovery into their training. It is absolutely essential. Hustle culture ignores all the science and data around rest and recovery. It assumes the ends justify the means,” she says.
“A start-up is always a marathon, not a sprint. So you need to do what is necessary for endurance.”
Neumann has always believed that athletes make amazing business people because they know how to play in a team, pursue excellence, and to endure pain and setbacks. She now wants to find a way to get more athletes into business.
“One of the things I have noticed is how much sport has given me in my business life,” she says.
“Many companies don’t see this treasure trove of talent that sits within elite sports people. It is a market failure. I want to help fix that.
“I want companies to benefit from their skills. I’m actively working to make this happen at a larger scale than has been done before.”
She stresses her interest in the Angel City soccer club is an investment in, not a donation to, Natalie Portman’s cause, which is also backed by stars such as Jennifer Garner, Eva Longoria, Serena Williams, singer Becky G, Billie Jean King and Mia Hamm.
“On paper this is one of the best investments I have ever made. Put your capital to work to build the thing you want to see,” she says.
“The timing of this was perfect because never before have we had a confluence of things around gender equity, sports and women sport.”
She and Portman have been close friends since 8th grade.
“We were paired together when we were 12 at school. Our principal made us buddies. She is brilliant academically. She went to Harvard like me. We are both book worms and love learning,” Neumann says.
“She is a great friend to bounce ideas off and gives me wise counsel.
“There is something so special about a friendship that is 40 years old. There is an unconditional love that will always be there. She has a handful of friends like me who were there well before her life in the spotlight began.”
Love conquers all
Neumann met Jodie Auster, an Australian-born doctor, at a Boston Consulting Group recruiting dinner while both they were earning their MBAs at Columbia Business School.
“We both have non-traditional backgrounds to business. We are not afraid to follow our intellectual curiosities to a career that is a non-traditional path,” Neumann says.
“The defining word for both our careers is ‘Yes!’ We are not afraid if something doesn’t necessarily work out.”
But the trials they have endured in obtaining dual citizenship for Miles, who was born before marriage equality was legalised in America, have been truly testing.
Neumann is listed on Miles’ birth certificate as his legal parent, which should automatically grant him US citizenship as it would to any other child born abroad to at least one American parent.
But they are still waiting.
“We have been in bureaucratic purgatory for about 12 years. It hasn’t been resolved,” Neumann says.
She also describes the adoption process she went through for Miles as “very demeaning”.
“You are the first person to hold your child when he’s born and you have raised that child. To then go through an adoption process where you have a social worker in your house, observing you and reporting like ‘Miles seems to have a bonded relationship with Rachel.’ No sh.t. I’m his mother,” she snaps.
“The whole thing was an exercise in bureaucratic box ticking and was highly offensive.”
Neumann became an Australian citizen 18 months ago to ensure they now have at least one citizenship in common for the family.
She now wonders whether they will even bother pushing for Miles’ US citizenship.
The family’s retreat from the world in these difficult moments – and to de-stress generally – has been a farm they purchased in 2017 in the Macedon Ranges outside Melbourne near a tiny town called Bullengarook.
The catalyst for the move came one morning when Neumann and her children were watching an ABC TV program titled Dirt Girl.
“When she signs off she says, ‘Don’t forget kids, get dirty’. I just had this visceral reaction that my children – who at the time were probably one and five – had nowhere to get dirty like I used to,” Neumann says
“I know this is crazy, but at that moment I said ‘I think I need land’.”
The family now goes to the farm most weekends.
“To me, it represents an opportunity to think outside the box and literally go and be in land. It represents giving my kids the freedom that I had to explore and get hurt, be dirty, and be free,” she says.
Neumann can never bring her brother back. But his memory has inspired her in the decade since his death to never waste a day.
“Losing a sibling is like losing a limb. It is such a terrible loss, especially when it is unexpected and when he was so young,” she says.
“It is now 12 years since his passing. Over time, I’ve realised that life is short and unpredictable and it is about how you spend your time in the moment.”
She still recalls thinking to herself in the week after his death “This isn’t fair, why did this happen to me?”.
“And then my inner voice quickly said, ‘Well, who should happen to deserve this?’,” she says.
“Life is all just a game of chance. S**t happens and you just have to figure out how to live through it. “
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