Kassar Taleb worked in early education for 18 years before studying the University of Melbourne’s Master of Entrepreneurship in 2017. Since then she’s been growing Shiftsimple, the startup she founded as part of the program, and part of that growth has involved being accepted into one of Australia’s leading tech accelerators, Startmate.

Hear from Kas about her experience, and how the good times at Startmate helped her navigate the tough times of startup life.

“Congratulations, out of 279 applications, you’ve been selected for Startmate Melbourne 2018.… keep your whole week of July 9 (2018) clear for a Startmate Week 0 offsite.”

Clearly this was an amazing achievement for us and for our startup Shiftsimple, a platform that connects regulated care services with an on demand workforce of pre-vetted quality talent, in under 5 minutes, every time, starting with the education and care sector.

My co-founder was nothing but ecstatic! However, I myself couldn’t help but feel a slight sense of dread among all the excitement.

I just kept thinking ‘How on earth am I going  to spend the next 12 weeks working with complete strangers — and spend an entire week 24/7 abroad with them!’ As an introvert I’d always enjoyed working alone, but my focus, coupled with the realisation regarding the immense opportunities that would come our way by taking part in Startmate, allowed me to forge ahead — excited and determined but, honestly, still a bit worried!

Where it all began

My entrepreneurial journey started in 2012. I was sick of living from pay cheque to pay cheque so asked my sister for a 15k loan to start my first company. With her investment, I founded an education and care service. My mission was to build a community of educators to support and train so they in turn could start their own childcare service from their homes.

We helped 372 educators in five years with an investment of $15k. I promised my sister that I’d double her investment and give it back to her within 12 months.

I did. Within 6 months.

(Interestingly, Andreessen Horowitz invested $20 million in wonderschool— so they’re doing the exact same thing I did but with 15k — go figure!)

I started to think, heck, if I could do this then launching Shiftsimple should be a breeze! I had a co-founder, we had just got into reportedly the best accelerator in Australia, so what could go wrong? In short — EVERYTHING!

A glitch before it’s even begun

On day 1, my co-founder and I were at the Startmate meet‘n greet night when we received an email from our remote tech team stating they could ‘no longer work on developing our platform’. That day was our platform deadline.

We knew they had been running behind schedule but for them to stop work entirely was a complete shock. The problem we faced now was having to tell our Startmate partner that we didn’t have a product; the tech platform that we’d been working on for the past three months was a bunch of screenshots devoid of coding.

We were, essentially, back to square one.

We held our breath and nervously told our partner and the support we received was nothing short of amazing. Immediately, he offered to introduce us to new tech teams. The very next day, we had half of the cohort and some mentors offer suggestions on how to automate processes which meant that we could begin the hunt for our new tech team.

A problem shared really is a problem halved, and in this case, a problem solved! Sharing our lowlight with the Startmate cohort helped us gel. It was incredible to watch. I began to completely rethink my belief that working alone was the only way to go.

Sharing your goals to help keep you accountable

Each week at Startmate, we took part in an exercise called ‘All Hands’. This involved standing up in front of everyone to share our goals, achievements, misses, etc.

What did I think of ‘All Hands?’ I dreaded it! Initially. But I was wrong.

‘All Hands’ at Startmate was not a place for judgement or negativity. This was a place where people held you accountable, pep talked you up, and kept you moving.


The 2018 Startmate cohort, from Kass Taleb

As entrepreneurs, we understood each other’s journeys and we held each other accountable. Accountability is so important at the early stage. We were so full of unknowns, self-doubt, and in many cases loneliness. We were launching different kinds of startups but found a deep connection in the fiery pursuit of our goals. We identified with each other’s emotional rollercoasters of being founders.

Something clicked for me. The Startmate team, my peers, the people around me facing similar challenges — I will always need that calibre of support and accountability. People I can call anytime to give me the talk, to sustain my belief and my action and those moments when I start to feel like an imposter or like I can’t make it.

The tide had turned — all of my hesitation and fear surrounding Startmate had vanished. I was a convert. I had found my tribe.

Surely after our tech team dropped out at the last second nothing else could phase us? Wrong. Very, very wrong.

Facing the reality of becoming an unexpected solo founder

Six months weeks into the Startmate journey and my co-founder and I had to part ways due to her visa complications.

As you can imagine, my stress levels increased, and my confidence plummeted — think massive imposter syndrome. How could I ever do this on my own!? Yes, I had successfully owned and operated an early education and care service and developed and sold a childcare centre, but all my past successes had been anchored to my specialty: education.

In this new role, as sole founder, my role increased exponentially, and I felt I couldn’t pivot off just my experience. I was now dealing with tech development, financial projections, pitching, raising — all new to me.

But, when the universe knocks you over, you can become undone, retreating to lick your wounds and rebuild your story along familiar lines. Or, you can choose to evaluate your priorities, be pragmatic, make choices, and break ground on a new, more promising path that looked nothing like what you had envisioned for yourself.

I was able to choose the second option because of the support I received from Startmate. They were there for me every step of the way and even when I felt like I couldn’t continue, there was always someone there to pick me up. I will never forget how incredible everyone was. Their support blew my mind.

The lesson learnt?  Believe that people will help, just ask.

I sharpened my focus on a course of action. I channelled my frustration into energy. When things went sideways, this energy became the fuel for my creativity and drive.

I had to give Shiftsimple the best chance at surviving. I started the hiring process and within a fortnight I had found a CTO, Head of Operations, Customer Success and Talent Acquisition. I had a team! A total brand revamp followed and we were ready to take Shiftsimple to the next level.

Whenever I needed help or advice, I reached out to Startmate mentors that had expertise in areas that I lacked and soaked in as much knowledge as I could. From tech development through to raising, they were all available to pay it forward.

This is what being a part of Startmate felt like:

Every day, you’re short of money, time and, if you’re not careful, imagination. The cognitive load of launching a startup is huge. You’re making decisions under pressure but having leading founders, investors and other inspiring guests come out to share their experiences kept me grounded and inspired to continue on this journey.

As I grow my business and rise as a leader, I will raise my mic, extend a hand always and pay it forward for those who don’t yet have a voice. Even if Shiftsimple doesn’t turn out to be a global company (it will be), I know I have accomplished something far greater than that for me. Startmate helped me break free from all of the barriers and walls I put up around myself that told me I couldn’t do it.

I now know I can and I will.


Wade Institute of Entrepreneurship  is a leading centre for entrepreneurial education. We deliver programs to accelerate learning, creation and connection, including teacher professional development programs, UpSchool Workshops, the University of Melbourne’s Master of Entrepreneurship, investor education program VC Catalyst, and bespoke program offerings. Learn more or enquire now.