Why It’s OK to Start a Second Start-Up (While You’re Still on Your First)

Less is more? Not always, says double start-up founder Taryn Williams.


It’s an indisputable fact: starting a start-up is a hell of a lot of work. There are late nights, early mornings, endless emails and that’s before you’ve even got your website off the ground. Some may wonder where someone like Arianna Huffington gets the puff for another job in addition to her mega media conglomerate but she did. Why would you double the hard work of one business to start another?

We asked the founder of WINK Models (and later, the start-up success of theright.fit), Taryn Williams to shed some light on why two can be better than one when it comes to businesses.


You started theright.fit alongside running an already successful business – why did you decide to take on another venture?

I fell in love with building tech platforms during the development of the WINK app. I just loved seeing how I could solve problems and build a scalable business through utilising technology. I recognised the changes in our industry, and saw a way to disrupt the industry by systemising processes and creating a market network. Some people think I’m crazy, or a glutton for punishment, but I think I’m just always looking for new ways to learn, grow and challenge myself.

What are some of the benefits (and downsides) to juggling two businesses?

The two, are complimentary, but also very different. They do in some ways, feed one another, so both win from the mutually beneficial alignment. That said, personally, it can be very difficult juggling two businesses. Earlier this year I made the decision to put the majority of my time and focus into building theright.fit. This meant taking a step back from WINK Models and allowing someone else to run it. Not an easy decision after being so hands on for the past nine years but something that had to happen. I am fortunate that I could promote from within knowing that the business will thrive under the direction of Sage Greenwood, WINK’s managing Director.

I’m also very clear about my commitments, and that it involves making sacrifices in my personal life to get two businesses thriving. It can be tough, but I love what I do, and wouldn’t have it any other way.

What are some of the skills that came easier your second time around considering you’d built a business before?

Definitely learning to delegate – this time I hired a full team from day one, and got the best people around me that can do a much better job in certain aspects of the business than me. I’d learned that the hard way with WINK, and it made theright.fit a much faster & easier journey.

What should people consider before trying to take on a second business venture?

You need to have a great team in place in your first business, and ensure the systems, processes and structure of reporting is clear before you take your eye off that company. Your team need to have the skills and resources to thrive without you, so it takes time to make yourself ‘redundant’ in the company.

What’s the most challenging part of the funding process and how did you overcome that?

I think the most challenging part, for me, was just being really, really clear on what we wanted in terms of investors, and not wavering from that. We had to really stick to our goals in terms of looking for long term strategic partners, who added value outside of just capital. Staying true to that, in the heat of the moment or under a lot of pressure, can be tough, but it really makes a big difference long term.

Arguably funding is a major first time obstacle when beginning any business. What do you think the single biggest hurdle to getting a yes from an investor?

I think it really varies from investor to investor. Some may simply not be taking on new investments at the time. Others may not be knowledgeable in your field, or not feel like they would add the value you are looking for. I think you can always ask for feedback on why they declined, and use that to improve your pitch or presentation for next time.

Obviously you’re looking for money from investors, but is there anything else you want from your investors?

I think it’s incredibly important that your investors bring much more than just capital. We were looking for strategic partners who also had marketplace expertise, establish contacts & networks in our space, and who would be a great sounding board for us as we grew. You also need to really be agreed on what success looks like – and being very clear about that from the start is important, and look for someone whose vision is aligned with yours on that front. You also want to respect them – it needs to be a really healthy mutual respect for you to succeed.

See Taryn speak at Kick. Start. Smart. on August 19th in Brisbane.


Oh, love this. So far the world says NO, two business are stupid and I don’t mind looking stupid, but I do appreciate someone that can lessen the pain hah! I want to do another project and around 3yrs into my first so more time on this project. For me, It’s there just simmering away and just a matter of time till I start the next “thing” this article has given me some things to consider and acknowledge before “jumping in again”. Thankyou.


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