Startup Advice

How founding and selling six startups taught Adir Shiffman the importance of luck, failure and humility: “My biggest risk was dying without being happy”

Angela Castles /

Adir Shiffman

Adir Shiffman, executive chairman of Catapult Group. Source: Supplied.

Adir Shiffman wanted to be an entrepreneur from a young age, but after leaving a career in medicine and founding and selling multiple startups, he now knows the entrepreneurial journey is more challenging, humbling and random than it seems.

Speaking at LaunchVic’s Yeah Nah conference in Melbourne last week, Shiffman shared the importance of acknowledging your strengths and weaknesses as a founder, drawing on his experience as the founder of of six startups, including PricePal and HelpMeChoose, and as executive chairman of $287 million global sports tech startup Catapult Group.

After being passionate about entrepreneurship as a child, Shiffman went on to study medicine, but decided to leave his “repetitive, bureaucratic” job as a doctor to pursue startups full-time.

“I had this epiphany that I needed my Monday mornings to feel as good as my Sunday mornings,” he told the audience at the conference.

“Everyone said it was huge risk leaving medicine and doing startups full time, but my biggest risk was dying without being happy.” 

After being involved in a range of startups — “ten of which worked, 35 of which didn’t work” — Shiffman said he took on his latest challenge as executive chairman of Catapult Group after “realising how hopeless I was at such a large number of things”.

Shiffman’s position as executive chairman only came about after a series of “horrible experiences” during the global financial crisis (GFC) taught the entrepreneur his strengths and weaknesses as a founder.

“I learnt good lessons in horrible ways,” Shiffman said. 

“I learnt that finance is quite important, and cash is quite important … I sold my company at the end of the financial crisis, and realised there’s an awful number of things I’m really terrible at.” 

After Shiffman sold HelpMeChoose to Mortgage Choice in 2010, he went through a period of soul searching.

“I realised that all the things my self worth is attached to I’m actually really hopeless at, so I had to really appraise my sense of self worth, which is not an easy thing to do,” he said. 

This period of self-reflection eventually led Shiffman to realise that “day to day leadership” of a company wasn’t suited for him, and that he should “never do something alone”. So when Shiffman was approached by the team at Catapult Group, he suggested he come on board in a chairman role, rather than as chief executive of a business that now employs 300 people globally.

“If I hadn’t have had those disasters and that self reflection, I wouldn’t have been prepared to admit to myself that I should not have been the CEO of that business,” he said. 

Why founders shouldn’t take startups too seriously

“The higher you get up in the organisation there are no good surprises,” Shiffman said, acknowledging that as a founder he sometimes “felt like everyone was against me.”

 Shiffman’s key advice for dealing with the pressure-filled environment is simple: treat it like a game. 

“I realised it’s all just a game, and the aim of it is to have fun,” he said.

 “We just play the business game where we need to score enough points to eat and have a house.” 

Shiffman’s past experience as a doctor taught him that the startup world “isn’t that serious” compared to the life-and-death nature of medicine.

“When I wake up in the morning nothing is going to kill me. When I was a doctor I saw people die; no one’s died in business so far with me.” 

Dealing with failure and regrets

Shiffman told the conference he deals with regrets and failures on a daily basis, and treats them as inevitable learning exercises.

“What do we all have in common? We have all made horrible decisions and will make horrible decisions in the future,” he told the audience.

“You just brace yourself for the daily catastrophe and get on with it,” he said.

For founders who are reeling after a bad business decision, Shiffman said the best thing they can do is “try to figure out why it turned out badly, then make different bad decisions in the future”.

Founders who may be celebrating success should be similarly humbled, Shiffman said, because success can be “problematic”.

“Don’t fall into the trap of thinking, ‘that worked well because of these four things’, when in reality it probably worked well despite those four things,” Shiffman cautioned. 

“When things worked out well I thought too much of it was due to good decisions I made, when in reality it was circumstances and luck.” 

Luck plays a vital role in the startup journey, Shiffman said, which is why he advises startups to appreciate the value of humor and “having a laugh about it” when times get tough, rather than accepting responsibility for every negative result.

“Luck is this universal thing; you’ve got to accept it plays a very fundamental role in our lives, and we should not be too earnest on how much we contribute to outcomes,” he said. 

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Angela Castles

Angela Castles is a Journalist at StartupSmart with a keen interest in the legal issues startups face. In her free time she can be found eating sushi and seeing live music.

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