Linking startup success with self-worth is disastrous, says entrepreneur Jamie Pride


Serial entrepreneur and venture capitalist Jamie Pride

Having birthed more than half a dozen startups and steered some of Australia’s biggest corporates, you’d think that Sydney’s Jamie Pride has much to say about success. Instead, the serial entrepreneur, venture capitalist and self-described ‘misfit’ is more interested in discussing the personal toll of failure.

Noting the high rate of startup failure in Australia, Pride – a mental health advocate – said that while entrepreneurialism can be “hugely rewarding”, founders should separate out their identity and self-worth from the success of their business.

Pride, formerly a Partner at Deloitte and the CEO of realestate[dot]com[dot]au, has founded or co-founded several startups including educational institution The Founder Lab, peer support network The Founder Circle, venture fund Phi Digital, HR management platform REFFIND, startup accelerator Digital4ge, and customer engagement consultancy Velteo.

He spoke with Dynamic Business about his interest in creating and supporting startups, the common thread between his business endeavours, the ‘toughest’ moment in his career, his desire to see more experienced entrepreneurs giving back to the startup ecosystem and his current focus in business.

DB: What led you to switch your focus from corporates to startups?

Pride: I’ve always been a misfit, I guess. Despite an extensive corporate career, I’ve always been drawn to startups due to the ability of founders to make a real impact – both to their business and potentially to society. I also think working as an entrepreneur is a great crucible. I believe there is no better way to understand yourself – both your strengths and your failings – than to launch a startup. It is a rollercoaster ride and not for the faint of heart but it can be hugely rewarding.

DB: What has been the common theme throughout your career?

Pride: At a general level, I find that the businesses where I have an authentic connection to the problem are usually the ones I am most passionate about. I recently founded a not-for-profit called The Founder Circle that focuses on targeted research, education and free peer support for founders who are feeling isolated or who are suffering from depression or anxiety. I love this business because I am so passionate about the problem we are addressing.

On a more specific level, I tend to be most drawn to business-to-business (B2B) Software as a Service startups. The first reason is that it’s an area I have a lot of experience in, having worked for SalesForce.com. Secondly, I find it’s often easier to address the B2B segment than B2C (businesses to consumer). There are some amazing B2C businesses out there but creating one that’s successful requires a lot of capital, timing and luck.

DB: What is your take on Australia’s startup and VC ecosystem?

Pride: I believe the Australian startup ecosystem is going from strength to strength, both in terms of the quality of the founders and the quality and experience of the VC community. That said, I still think there is an opportunity to better support founders, especially founders just starting out who may have a distorted view of what lies ahead on their journey. I would like to see the more experienced entrepreneurs in Australia giving back to the ecosystem – not just through funding but by providing mentorship and advice. In terms of the local VC community, I think it is unbelievably collaborative and starting to mature. Although the terms being offered by VCs are more founder-friendly than ever, I would like to see VCs take a more involved approach to supporting their founders through coaching, education and advice.

DB: Are you able to pinpoint a key defining moment in your career?  

Pride: There have been many, but my last startup failure was probably the toughest. It was pretty public and painful. It was a defining moment for me because it allowed me to reflect on the personal impact startup failure has on entrepreneurs and what kind of support they need. Also, it got me thinking about how we contextualise failure as a country – it is still very stigmatised. The US, by comparison, has a better attitude towards entrepreneurial failure – it is almost seen as a right of passage. As a result, I started studying why startups fail, which led me to write my most recent book Unicorn Tears – it explores startup failure and proposes new ways for entrepreneurs to think about the skills they need to succeed.

DB: What advice do you have for startup founders around failure?

Pride: You are going to fail and that’s ok. I’m not saying start with failure in mind, but I am saying be sure to separate out your identity and self-worth from the success of your business. While most entrepreneurs think and work in their businesses 24×7, it’s important for them not to “be” their startup. When I see entrepreneurs suffering from mental health issues, or down in the dumps, it is often because they have closely linked their startup success to their self-worth. In an environment of high business failure that is a recipe for disaster.

DB: Do you have a mantra that you live by in business?

Pride: Capacity outweighs capability, entrepreneurialism is a marathon. While developing skills is important, having the capacity to go the distance is crucial. As a founder, that means constantly working on your awareness, adaptability and resilience and building up a level of “founder fitness.”

DB: What is your current focus as an entrepreneur and VC?

Pride: My current focus is very much on sustainability. Given the volume of new startups (approximately three startups are founded every minute) and the high failure rates (92% fail), I am very much focused on how we build a sustainable ecosystem. That means finding ways to failure-proof founders, make them resilient and keep them coming back for more.

Also, I’ve just started a new venture fund, Phi Digital Ventures, and I’m looking to make 10 to 20 investments of around $100k in seed-stage technology companies this year. Similar to the 500 Startups model in the US – but with a more local and targeted flavour. Despite the risks, I am passionate about investing early in technology companies – where the valuations are more realistic, and where my team can make a real impact and get the businesses off to a good start. So, I am on the road again looking for investors in the fund and great founders and startups to invest in.

Related: Why Jamie Pride is helping organisations deliver the staples of workforce engagement with REFFIND and The ten reasons startups fail.