What I learned from interviewing 100 business owners

This is the title I will be writing with a sense of relief in 32 interviews time. ‘Why are you interviewing 100 people?’ is the most commonly asked question and the short answer is, it was the number that seemed on the edge of impossible when embarking on this journey back in January 2016.

‘Interview 50 business owners’ I said inside my head, letting the words form into a critique. ‘50 is easy’. ‘50 is do-able’ came back the reply.

We all like to think we’ll reach the age of 50 at some point, but as a challenge it seemed half baked, like a halfway marker and not an ultimate goal. ‘One hundred.’ Now that had some weight to it. ‘One hundred.’ I repeated. It struck a little fear into me because 100 has heritage, one that even the Queen signifies with a congratulations letter to anyone who manages to store up 100 years of wisdom on planet earth, yet it came with a mortal risk of failure.

Counting To One Hundred

You may remember counting to 100 growing up. ‘Can you count to 100?’ was the ultimate childhood friend challenge and when someone took up the challenge, your buddies would quieten a little, and gather a little closer to hear if you could get past 20, to listen to how you pronounced numbers past 50 (while they tried to memorise a few) before finally hearing the slowed repetitive declarations of those rare numbers between 80 and 100 . Yes, there was the easy rebuttable ‘1, 2 miss a few 99, 100.’ and that would get a few laughs amongst our easily amused kid minds. But when a kid took on the challenge despite the fear of being laughed at for only making it to 40, or 63 or 75, that was a moment worth experiencing.

Public Accountability Improves Shipping Quality

As soon as I’d completed the handshake with my better self to accept the 100 Interview Challenge, my mind raced to find ways of escaping out the side door, turn back and escape through the recently formed entrance to shelter from the downside of an incomplete race. ‘See how you go, you could always just do 20.’ This is what fear of failure does, it rationalises the shortcuts or the failure so you can reframe it and protect your fragile pride. I had to come up with a way of lancing that out clause entirely, which I came to regret more than once over the next 12 months when it got tough.

Each interview would be a raw audio cut that captured the essence of the chat, and to satisfy being accountable to the public at large, I set the following rules:

1. There will be no editing.
2. It will go for at least 20 minutes and as long as it needs to.
3. You will start every intro with “This is the Ryan Marketing Show, and you’re listening to episode x of 100.”

January 19th 2016. The race to 100 had begun.

Finding your Limits

I’ve always loved numbers, and later on in my early teens I would perform mental aerobics while being driven around in the back of Mum and Dad’s car, using the number plates of cars as my palette to add, subtract and divide. It would have been a natural assumption then, that when I was accepted at Victoria University in Wellington, that computer science would form part of my double degree aspiration. Unfortunately, that’s where the math ran out, because although my brain was well trained in flipping multiplication and division faster than most (a skill that came in handy working at my Mum’s florist shop) it turned out to be less memorable when applied to the rigours of algebra and calculus.

Getting too comfortable

In 2016, I felt like I’d hit another limit that needed pushing through. I’d gotten too comfortable. Comfortable with my clients, comfortable with my marketing skills and comfortable living in Hawke’s Bay. ‘Homeostasis’ is the tendency towards a relatively stable equilibrium between interdependent elements, especially as maintained by physiological processes, yet this body state doesn’t encourage growth and we’re happiest when we are living life with purpose which usually involves challenging ourselves.

It was my own fault

In 2010 I had completed a two year stint running a learning & development media agency in London. Our office was on Great Titchfield Street near Oxford Circus and in one of these multi-tenanted office buildings now referred to in the more fashionable tones as a ‘co-working hub’. Our opposite neighbour was a company called Spotify with 7 employees and we all revelled in the aura of being in the offices that MySpace started out in. In the basement was a purple neon lit bar with white leather couches which we adopted for client meetings because it was free and rooms cost by the hour. That was in London, and so on returning to New Zealand I had to decide what I wanted to create here in Hawke’s Bay which ultimately led to a way of life that got too comfortable that laid the foundation for the 100 Interview Challenge. Here’s how it played out.

Make your situation work for you

Building a business means making your situation work for you not against you. On arriving in Napier, New Zealand, I didn’t want to build another body shop of creatives. I wanted to spend time with my son Joseph with a little consulting work in between, learn some new business industries, enjoy the Bay’s food and wine scene and generally kick back a bit. I enjoyed that time so much, and while I prioritised family over career, it became my de facto New Zealand way of life. I made things. I chatted with chefs passionate about what they did and wrote about it. There was something truly fulfilling about prioritising making things over managing people, resourcing projects or filling up calendars.

By early 2015 all of my clients except one was fully remote and the one that wasn’t remote was at a brewery, on a Friday. The very situation I had aspired to create had been attained, and yet I was unhappy. Jeremy Rameka from Pacifica Restaurant once said to me ‘be careful what you wish for.’ I asked why, he replied ‘you might get it.’ No matter how comfortable my situation was at the end of 2015, it wasn’t what I wanted so it was time to mix it up.

The 100 Interview Goals Then

The goals that I started out with are not the goals I have now, and I imagine they may change again by the time I reach the 100th interview. Initially the were:

Showcase the latest in digital marketing techniques through the voices of business leaders in our community.

Give business leaders a platform to tell their story long-form in a way that leaves a memorable impression on the audience.

Create a community of 100 like-minded business leaders that from a broad cross section of industries and sizes of business.

Provide outsized value with no expectation of anything in return.

These goals were business centric except the last one. There was never an expectation of payment for being part of the project. Reciprocity did come in other unexpected ways that enriched my life far more than being paid could have, which I’ll cover later.

The initial goals have been met, and continue to evolve. The complexity of the digital marketing techniques applied have grown, the number of publishing channels has extended from Soundcloud to encompass iTunes, YouTube and a Netflix style site my development house built to host all of the episodes.

At the halfway mark, I invited all 50 of the business leaders to a lunch at Ten24 restaurant, hosted by chef Kent Baddeley from Episode 3. This was an invitation to celebrate the halfway point in the interview journey because too often in business (and life) we don’t celebrate the journey as we get too focused on the destination. From those I’ve met so far, they often look back warmly on times when their own business journey was the least clear while they were the most determined.

Although I started interviewing friends with businesses, I knew that at some point I’d run out of friends to interview (that turned out to be around Episode 15). It was also about this time I had my first double crisis of confidence.

please leave a comment below with your feedback. This is draft one :)