From A Simple Social Enterprise Idea to A Successful Side Hustle: The Story of Wild Tiger Tees


It’s easier today than at any other time to start something and make a social impact. But there’s a catch. Most of us can’t afford, at least at the start, to quit our day jobs and take up our social projects full time. They usually begin as a side hustle, and with the side hustle comes the risk of overload and sinking under pressure. In this article, I take you through the story of my own side-hustle, Wild Tiger Tees: the excitement, the success, the near-drowning, and the story of how I got back on deck, and how I turned a social enterprise idea into a business that makes a big impact now.

How I Developed a Social Enterprise Idea

In 2017, I had Ann Bischoff as a guest on the People Helping People Podcast.  Ann is from the Star House, a day center for youth experiencing homelessness. Something struck me about the situation that these youth face – especially the life circumstances that they never chose. I had such a supportive family growing up, and still do today, and I can’t imagine life without that. Especially at age 16 or 18, I can’t imagine having to make it on your own without any support.

I walked away from that podcast, wondering what I could do with the Star House. About a month later I was listening to the Joy Venture Podcast and came across a story about a button club that someone had started as a hobby, which then grew into something. That gave me an idea: perhaps I could start a t-shirt club, with t-shirts printed by the youth at the Star House. I’ve always wanted to screen print my own t-shirts, and I couldn’t stop playing with the idea.

The Implementation of My Social Enterprise Idea

I knew I couldn’t do it on my own, but I started researching social enterprise ideas and talking to people (pretty much everyone!).  Then I took my idea to Give Back Hack. This is a startup hack-a-thon style event, where people come together on a Friday night, pitch social entrepreneurship ideas (a lot of ideas!), narrow them down, and then build a social impact business around it over the weekend.

My idea was selected, and a team of about 10 enthusiastic people was formed. It’s amazing what you can get done in a weekend! We formed a team and have been meeting regularly to get our pilot off the ground. Right after Give Back Hack, we jumped into SEA Change – a social enterprise accelerator. It’s like Give Back Hack, but more in-depth, and spread over 12 weeks, with each module covering a topic that we focus on for our business. In a team with diverse backgrounds, this has helped us develop our business plan together.

It was a great resource and helped us as we launched our pilot.  We’re now in our second year of operation, and Wild Tiger Tees is starting to take shape.  This year we’ve been focusing on sales to grow and expand our program, but it’s challenging when this is a side hustle, and there’s so much to do to maintain momentum.

The Art of the Side Hustle

What is a side hustle?  It’s a term for careers that people start alongside their day jobs, often bootstrapped with income from said jobs.  Sometimes a side hustle is only ever intended to be that.  For others, it’s a stepping stone.  It means they can keep their day job as a backstop, while slowly building the foundations for, and then transitioning into, a career of their own design.

Wild Tiger Tees is a great example of a side hustle. All of our five founders had day jobs, and we ran our work program once a week on Friday nights. Since October 2019, we’ve been working 2-3 nights a week. While we are technically profitable, it’s not even in the ballpark of the type of sustainable profit that might warrant us leaving our day jobs or hiring employees. But it’s fulfilling work, and personally, I’ve grown significantly from building my own company.

There is an art to managing a side hustle.  It’s a balance.  There is a lot of communication that happens during business hours, so meeting with people, calls, and follow-up e-mails happen during breaks, over lunch, or in the evening.  My day job is busy as well, and sometimes spills over into the evenings and weekends, and my hours are flexible as long as the work gets done.  But when the day job calls, it generally has to take priority, making it harder to run and grow the side hustle.

Man Overboard!

There are two sides to starting a business venture: what goes into the venture to make it successful, and what goes into you.  And they’re both equally important.

In my life, one of the biggest impacts has been on personal time. Between my day job, the side hustle, and family life, quite often, there wasn’t enough time for myself.  It nearly sent me under. 

When I started Wild Tiger Tees, I had no idea what I was getting into.  I just pushed myself on and on, trying to figure out how to sail my ship across a great ocean without ever having taken a proper sailing course in my life.  It didn’t go well.  Yes, we got most of the pieces in place, but there was still a gaping hole – how to generate sales!  It didn’t help that my day-job picked up momentum as well, so not only was I trying to sail a new ship, but I was driving the day-job bus as well.  And instead of my normal route, I was now driving three routes at the same time.  It was a bit of a stretch.

Side hustling is No Joke

On the personal front, I was a disaster. While the company boat was chugging ahead, I fell off and almost drowned.  I managed to make it back to shore, but I’m still drenched, and exhausted from all the swimming.  That’s because I forgot to balance what I needed along with what the venture needed. I need rest and creative inspiration. 

It’s interesting what happens when you push yourself past your limit. Your body reacts to situations more harshly, and you respond in ways that aren’t always productive.  My unconscious survival technique was avoidance.  But avoidance only compounded the problem, making it worse.  Everything began to pile up so that, in addition to sailing a ship and driving a bus, there was a back-log of stuff always waiting to be unloaded at the pier.

Getting Back on Deck

The point is that it’s easy to forget to create personal time to relax without an agenda or a plan, to make space where you can remember what it’s like to be, and especially to be bored.  You need space like that where you can dream and imagine.  It’s these dreams and imaginings that fuel the rest of your creativity and insight, and when you sacrifice them, you get stuck in a world of doing, doing, doing, which will lead to burn out at some point.  You need to recharge.  How you do that is different for everyone.  But you need to make it a priority.  Something new I’ve been trying this year is to meditate for an hour in the morning and an hour in the evening.  That leaves me with even less time but is quite centered and helps me make more effective use of my time.

So one of the biggest lessons of keeping a side hustle is the need to maintain balance.  I’ve seen it in my own experience.  I’ve heard Jay from the Unreal Collective talk about it, and Anna Hetzel from her copywriting business.  One thing that they do to help them keep their balance is to audit the activities in their life, and cut out any commitments which aren’t essential to their path.  Community organizations?  Talks?  Sports or dinner expectations?  Any planned event that doesn’t align with your core missions, needs to be cut.  Focus on what’s important, make sure that you’re making enough time for yourself, and you’ll thrive.

At the end of the day, starting a new venture is hard work. But you need to remember to give as much attention to yourself as you do to the venture, or you’ll find yourself drowning at sea.  Stay fit, so you can swim and get back on deck when the waves knock you off.

A Strong Heart

Starting a social enterprise is not for the faint-hearted. At the end of the day, it is a business, just like any other. There are sales channels, business requirements, sourcing, scheduling, and it goes on. It’s easy to get overwhelmed, but the rewards are immeasurable.

The main thing that keeps me going is the youth that we get to work with.  They are incredible, and I feel it’s such an honor to work with them.  For me, it’s enough to know that what we’re doing is on the right track, even if we still have a long way to go.

My Biggest Takeaway

It’s easier today than at any other time to start something and make a social impact. It’s not necessarily easy, but it’s certainly doable if you look after yourself, and it’s so fulfilling and rewarding.

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