Business lessons I learnt from launching my side hustle

First appeared in Stuff 30 May 2023

By Antony Young

So often you read about standout companies and entrepreneurs as they recount their recipes for success. But in business, just like in sport, you learn more from your losses than your wins. Some of our most notable sporting achievements came from the pain and lessons of some of our worse defeats. Think Graham Henry’s 2011 winning World Cup result after the disaster of 2007.

So I thought I’d share my experience. A sort of reverse brag. What can you learn when a business fails? A cautionary tale that might save you some pain, personal and financial, when planning a new venture or side hustle of your own.

My side hustle was launching a newspaper. It was a city news service dedicated to Wellington, delivered free via email. We published 17 issues and grew a circulation of about 10,000 subscribers. But I made the call to suspend it. In my eyes it wasn’t a complete failure, nor was it a success. Here’s what I learnt.

Is there a ‘market’ in the niche?

Often when you come up with a business idea, it starts with identifying a niche in the market. A need that isn’t being met with existing products. I felt a city of 400,000 could have done with an alternative news voice.

I was right. There was plenty of support and interest from readers. But the more important question I should have asked was, is there a “market” in the niche? How easy is it to get those revenues? How quickly can you get to break even and then to profit? For us, our model needed to be advertising funded, and when we went to the market, it was an uphill battle, particularly in the current economy. Which brings me to the next point.

The right time/idea

There are many great business ideas, but the trick is knowing when is the right time for that business idea. Back in 2001, I was offered a job with an internet media company that wanted to broadcast television content across the internet. But back then, the average download speed was under 1Mbps. It was just too soon for that idea. Often the time is dictated by your own personal circumstances. You’ve quit your job, or you just stumbled on the idea, but more scrutiny needs to go into whether this is the right time to enter the market.

For us, launching in a softening economy where advertisers were more cautious wasn’t the right time for our idea. The most important point here, is to genuinely look for the signals. Friends will always be supportive and positive. Ask the person who is going to be the most honest. I consulted with two trusted advisers who were going to tell me what I needed to hear. Find those advisers.

If something can go wrong, it will

When Mike Tyson was asked by a reporter whether he was worried about Evander Holyfield and his fight plan he answered; “Everyone has a plan until they get punched in the mouth.” You can spend months writing a business plan, and making it look pretty in PowerPoint, but count on several bruising body blows that can come from directions you won’t expect. For us, there were too many of these to include for this article.

Of course, you will be nimble, and no doubt shift tactics on the fly. But don’t let that throw your business plan out the door. The financials you worked on still apply, and you need to keep the same fiscal discipline no matter the business model. I think the main lesson here is be prepared to give yourself as much room on the numbers as things will always go slower than you expect.

Marketing is more than advertising

I spent many years in my career at the likes of Saatchi & Saatchi telling clients that advertising and generating awareness for your product is a key to success. If it was as easy as just throwing money at advertising, more businesses would flourish. But for smaller businesses, advertising is just one marketing channel in the toolbox. Personal networking, publishing content, tapping into influencers, publicity and social media in combination with advertising helped us to grow our subscriptions. A single post that cost us nothing in local Facebook page WellingtonLive delivered hundreds of sign-ups within a few hours.

Fail fast

One quality every entrepreneur seemingly needs plenty of is self-belief. One of the hardest things with your business is to admit you got it wrong. Many times your ego can get in the way of you seeing things clearly. But an entrepreneur needs to do the hard and necessary things. Our business plan had us break even after 20 months, and when those unexpected hits landed, we tried several things, but the trajectory wasn’t going to meet our financial goals.

You have to front up to the data when it isn’t telling you what you want to hear and regroup to fight another day. There were plenty of positives to take from this venture, but as a business it wasn’t going to work.

Passion project or business?

Reflecting on my experience, I did find myself asking, was our newspaper a passion project or a business? I guess it was both. And while that sounds dangerous to call any business a passion project, I believe that if you are passionate about what you are doing, then you increase your chances of success. Being passionate attracts great talent, engenders customers and makes it less a job.

As you would have gathered, I like to draw inspiration from sport, and so will leave you with one last gem. Last month, NBA basketball star Giannis Antetokounmpo was asked at the press conference immediately after his team was knocked out of the playoffs, whether he view this season as a failure. He replied, “It's not a failure; it's steps to success.” Time to begin planning for the next idea.

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