Lisa Messenger has one of the most impressive entrepreneurial histories out there. From founding The Collective, writing 24 books and being requested all over to headline events and conferences, Lisa’s expertise and experience is impossible to doubt.

Her recently released 24th book, Risk & Resilience, is all about the mistakes she’s made along the way, and how to escape falling into them again – a sort of motivational ‘how not to do’ of entrepreneurship.

We spoke with Lisa about about how she’s gotten so far, what it’s like looking back, her goals and her non-negotiables.

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I knew I had the power to disrupt the norm when… I was at school. I was always in trouble for asking “why”. It’s this same mindset that is celebrated today as an entrepreneur. It just has some more emotional intelligence and purpose behind it.

I knew all my entrepreneurial endeavours were worth the risk when… within 18 months of launching Collective Hub, Anna Wintour asked me to meet with her in NYC to ask how I was doing it. The print mag was in 37 countries, 18 months from launch. It was a wild ride (still is actually – just starting to pivot into a different form. The true test of any entrepreneur – can you move with the market needs and changing technologies/platforms?).

I am at my most challenged when I am… cash poor. When there is money flowing anything is possible. Whilst I couldn’t care less about money for moneys sake, it does buy freedom, choice and platform. And while I’m all about there being more than one currency, cold hard cash is needed to pay things like print bills.

It’s important to me that the message of Risk & Resilience gets out because… I think people spend much of their lives thinking bigger is better. Having been there, I can say it’s certainly not the case. A sustainable well thought-out business with systems and processes (especially as a creative) is an absolute imperative. This book is largely about the mistakes I made in the hope that others might heed my advice before they get into the same mess. It’s all about how I got into it, found my way out of it and am now happier and more on purpose than ever.

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My biggest motivation for writing is… to live my best life and share the lessons along the way. I vowed to be an entrepreneur for entrepreneurs, living my life out loud and showing that anything is possible. Whilst not always easy, I share it all in the hope I might help others to shine a light on what it’s really like to be an entrepreneur – the good and the bad – making it real, raw, relatable and attainable.

I’m at my most focused when… I am totally on purpose. Focus is a learned discipline. Anyone of us can self sabotage, get ‘busy’ or procrastinate. It’s a daily practice for me to focus.

Some early challenges in my career were… cashflow, getting the right team, working out what I was here to do on this planet, and staying focused.

At the time of starting out, the state of my finances was… non-existent. I went from a full time job on $63,000 to jumping out and taking the biggest risk of my life. That was 17 years ago and I’ve never looked back. I’ve had to learn to get intimate with data and financials. As a creative it is an absolute non-negotiable even though it’s kind of the last thing I ever wanted to do.

A financial habit I had to change was… looking at data daily, setting budgets, slicing and dicing everything. Sometimes the most fun things aren’t the most lucrative. So it’s a constant game trying to work out what to drop and what to keep. Sometimes the things I keep aren’t the most financially lucrative but they are the things I enjoy the most.

I managed to save / budget by… making a lot of sacrifices. I’d had my own businesses for 11 years before I started Collective Hub in 2013. But I didn’t pay myself for most of the past five years of Collective Hub and I sold two properties to invest into the business. Now (finally) it’s got a really stable base from which to build something really big. But I have sacrificed a lot along the way.

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My biggest goal as an author was… to lift other people up – to be relatable and attainable and to show the real story behind the story so others didn’t feel so alone.

I reached it by… well, I haven’t made it yet but I’m making a dent. Small unknown fact: I have written 24 books – but I think hardly anyone read the first 18. It wasn’t really until I wrote Daring & Disruptive in 2014 that my books took off and became best sellers. So the lesson… just keep chipping away and finally something will work.

I first felt like the venture was a success whenI saw Collective Hub sitting squarely in between Harpers, Vogue and Vanity Fair in news agencies piled high… that was a surreal moment of, “Oh my gosh – we’re really starting to do this.”

I celebrated my early wins by… probably going out and partying. Things have changed a lot since then. I take a moment to pat myself and my team on the back but then I keep going. It’s funny, the bigger things get the more you level out – I just keep going really. So many good things happen every day now that I don’t have time to get complacent. But it is important to stop and ‘smell the roses’. I’m about to go overseas for a month’s holiday so I probably go hard for big periods now but then take some true time out to recharge, refresh, recalibrate. Just time with me and my man.

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My biggest learning from founding The Collective Hub was… Bigger isn’t better. Sometimes it’s better to have a decentralised team of specialists not generalists on a project-by-project basis with specific KPIs and deliverables. My editor, Amy, has always worked remotely on a freelance basis even though she probably has the biggest job in the company. So I decided this is the smartest way to work moving forward. It’s good to keep a fixed cost base down so that you can be nimble and flexible and move with the markets, be able to pivot when needed. We needed to do this over the past 18 months and the restructure, whilst difficult, ultimately is the best for our community and our purpose.

The most life-changing decision I ever had to make was… Oh so many… Where do I start? But one was certainly to rethink Collective Hub. What I would say to this is know your purpose but don’t be attached to a specific delivery mechanism. I luckily said from day one that it’s irrelevant if it’s a print mag, online, social, speaking gigs, books, workshops etc – as long as we are delivering our purpose, the delivery channel can change. And for any business – needs to – constantly. Change is the only constant.

I still need to work on… not being too attached to what others think or say. Taking on the important stuff and letting the other stuff slide. Also being the best version of me. My health. Not getting stressed or anxious or living in a state of fear. Life is a constant education and one non-negotiable is that every day I work on myself. That will never stop and I can always improve.

My long-term goals are… to live a full life of adventure and to give voice to, and be a voice for, others to live their best life.

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If I had to give a budding entrepreneur one tip, it would be… surround yourself with an awesome team. Hire your weaknesses (eg. I am TERRIBLE at detail). Get intimate with your finances and data.

My theory for what makes a good business is… an unwavering self belief. Constant hard work. A sense of purpose. A great team. The ability to fail fast. The ability to get up again with a smile on your face and a fire in your belly when things don’t go to plan.

I maintain a work/life balance by… having rituals and routines and non-negotiables. Boundaries around my time. Health is my number one priority.

The best bit of advice I received was… fail fast.

Image: Instagram / @lisamessenger