Member preview


Tell me what do you for a living, without using your job title?

I spend my work days figuring out how ustwo can make a meaningful impact in the world through the process of company building.

That means providing a space for, working with and investing in startups at the moment. But an important part of my job is embracing change, so who knows what that will look like in the future.

Tell me your career story in three 1-stence bullet points.

  • I moved to Sydney for a job when I was 23, and I’ve never moved back to the US
  • I’ve always felt like I was a ‘soft skills’ person trapped in a ‘hard skills’ career path (audit, venture capital, management consulting, MBA)…
  • And now, at ustwo, I feel like I’ve finally found a place where my personal values are highly aligned with a company’s values

Why do you do what you do? What need (other than paying bills etc.) does your job fulfil?

Man, tough question. I’m the kind of person who assesses the quality of my life on relationships first, and career second, so in many ways my career is what gives me the means to cultivate and sustain those relationships (especially living so far from family). From my career, I look for intellectual challenge and opportunities to learn. I really enjoy helping people navigate their own careers and challenges, and that has become a big element of what I get to do now.

Describe the journey between where you are now and your first, full-time job?

My first salaried job (i.e., not hourly, part time) was right after university, working in the Internal Audit team at Fidelity Investments in Boston, MA. I lasted exactly 51 weeks before I was so bored out of my gourd that I resigned and took a job in Sydney, Australia as employee number 1 in a very small company hoping to become a venture capital player in Sydney. I realised then that I was actually a bit of a risk taker in my career (for someone who is otherwise a bit risk averse in my personal life). Anyway, that was 2007. The financial crisis hit in 2008, crushing any hopes of raising a venture fund. I really loved what I was doing at that time, but it wasn’t something I was going to be able to make a career out of.

Staying agile and crafty, I was able to eek out three years in Sydney before going to INSEAD, an MBA programme in France. I thought I needed a big brand name on my CV and a degree that would help me transition back to the United States to join a consulting firm. I got the brand name, and the consulting firm, but ended up in London and not back in the US.

I did three years as a management consultant at a firm called L.E.K. Consulting. L.E.K. is known for being very quantitative in its approach, and I always felt out of my depth on that front. I loved the variety and intellectual challenge of consulting, but I did not love the very long weeks and knew that I didn’t want to be a partner in a consulting firm. Seeing the signs of the times, I also knew I wasn’t going to develop operational or digital skills doing the kind of work that L.E.K. does.

So I drank the startup kool-aid and joined a startup called Hostmaker in 2015. I did 6 months and realised I was not meant to be in the hospitality industry. I got an introduction into DICE, a mobile ticketing app for concerts, through a friend and started there in August 2015. I had turned down a music scholarship at the University of Miami when I was 18, so being in and around the music industry was great fun. I spent two years at DICE, seeing it through a few fundraises, a little international expansion and doubling the team size.

Once I knew I was going to be a dad, I knew I needed to find something that was a little less risky than a Series A startup, and that’s when the timing with Adventure just worked out perfectly.

Where do you find your drive and your confidence?

I took a very long-term view on the opportunity to work with ustwo, eventually.

So, I don’t suppose that was confidence so much as a concerted effort to work towards something I really wanted.

In terms of deciding to leave DICE without a plan in place, that was pretty much a necessity. I resigned in Sept 2017, knowing I had a baby due in February 2018. I needed to make that career transition before I went through the biggest possible change of becoming a dad.

I guess I was confident I could make that transition because I had a very important reason to make that shift, and I had developed a lot of great experience in my career.

What advice would you give to a smart, driven 18-year old trying to get into your field?

As my ‘field’ is pretty nuanced, I’ll go with some of the best advice I’ve been given.

One piece was from my older sister, who told me when I was 22 that;

“Your twenties are a tough decade. People will place a lot of expectations on you to follow a certain path, hit various life milestones and know what you want. But you’ll still getting to know yourself and that’s okay. Relax, try to enjoy it.”

…And I did, I lived in 3 other countries during my 20s and travelled to so many more. I have no regrets about using that time to figure out what was important to me. I loved my 20s for a lot of reasons, but I love my 30s even more because I took the time to figure that stuff out.

The other best piece of advice came from a professor at INSEAD. He said;

“No one will care more about your career than you will.”

It was a really important message to hear and really digest because I see it over and over in the workplace.

You have to be your biggest advocate because no one else has as strong of an incentive to support you, as you do.

You may get support from great bosses and team members. But ultimately, they will also be looking after their own careers. It’s hard advice to deliver on, and I’ve certainly not always followed it.

If you could put your brain in the body of an 18 year-old who can’t afford to attend higher education, but wants to end up in your job… what might a rough plan look like?

There are always successful people who have not gone through traditional education routes.

Find them! Get their advice, work for them if you can.

They believe in your potential without you needing to have the university degree (and no, potential does not require a university degree).

Once you can find a network or environment that is based on merit and the quality of your ideas and work ethic, you can build your career from there.

We have someone on the Adventure floor who is a filmmaker, and he skipped uni and just started making films — short, small films at first.

He’s only 25 now, but he’s been making films for 7 years! People respect that experience more than if he had a degree from a great film school.

What is bad advice you hear being given about your job or your industry? What advice should people ignore?

One of the things that I dislike most about the various parts of the startup and creative industries that Adventure touches is the idea of keeping things secret.

I understand concerns about competition, but I think they are dramatically over-blown.

So much of what startups and creatives are doing require learning from one another and a network effect, in order to become successful. So, better to embrace that, in my opinion.

Tell me about a time in your career that you’ve struggled? Or felt lost?

When I moved from management consulting to startups, I chose to take a massive pay cut. (Like 33% of my salary type cut.)

That was a huge risk, and while at the big picture level it has led me to ustwo Adventure, I still feel I left considerable value on the table in the context of my career.

Beyond the financial impact of this, the struggle for me came to be about feeling undervalued by my boss. I knew I was delivering the same quality of work as I used to, that my level of output was well above the capability of many of my colleagues, but I didn’t trust my own sense of worth.

I allowed myself to be benchmarked by other employees — much younger, less experienced employees — and the broad argument that ‘startups have to stay lean’. That may be true to some degree, but I realised that good talent warrants appropriate compensation, even when running lean.

While I was in the role, though, I kept accepting those circumstantial excuses, and ultimately it lead to a deterioration of my confidence in my work, my self worth, and my sense of belonging in the company.

Tell me about a mistake or an obstacle that you wish someone had warned you about?

I wish I had had a better understanding of the dynamics of being a startup founder vs. a startup employee.

It’s come to be my view that founders take on only slightly more financial risk than startup employees; however, they get much greater upside in terms of experience.

If you are the founder of a failed startup, I’ve observed you can call that failure learning and recover in your career more quickly. If you’re in a failed startup as an employee, future employers aren’t likely to see it as ‘learning’ or ‘succailure’. Despite the fact that you’ve taken enormous risks and been exposed to a lot of learnings.

Add in the fact that founders get equity and employees get options that come with all sorts of stipulations, and I think risk/reward profiles become very lopsided.

The result is that you need to think VERY hard about joining a startup. For many, it may not be all about finance and career marketability, so it’s not as simple as I’m making it sound. I just wish I had better warning about it.

What is the book (or books) you’ve given most as a gift, and why?

The most recent book I gave as a gift was East of Eden, by John Steinbeck. I just think Steinbeck is a brilliant author, and East of Eden is a terrific, sprawling work of fiction that rewards a reader’s effort.

Another, rather niche, recommendation is The Master and His Emissary by Iain McGilchrist. This is all about how the brain processes the world. It goes DEEP on how the left brain and right brain work, independently and together, and then the author boldly traces the last few centuries through the lens of how thinking patterns have shifted. For those who associate themselves with creative and holistic thinking, it’s an incredibly fascinating book.

Lastly, the other recent go-to recommendation/gift is The Silk Roads, which is an ambitious history of how the area broadly referred to as the Middle East (though it certainly extends into Europe, Africa and Asia at times) has played a crucial role in shaping today’s world. It’s just fascinating, and it’s a topic I really didn’t know much about, so I loved learning about it.

What was the last song you sang to yourself or someone else?

I’m singing to my 3 month old son a lot right now in an effort to get him asleep. Last song was ‘Oh My Sweet Carolina’ by Ryan Adams. He’s from North Carolina, like me.

If you could wake up tomorrow with one superpower, what would it be?

This one is easy: teleportation.

Justin Michaels is the Adventure Director at ustwo.