My Story with Generation Entrepreneur

Blake Im
19 min readDec 21, 2020

If you have personally known me to any degree in the last 2 years, you would know how much Generation Entrepreneur means to me.

Generation Entrepreneur is a non-for-profit education start-up striving to empower high school students with entrepreneurship skills, running in-school workshops as well as holiday hackathons.

I joined the company right after I finished high school, a year after I first got to know them as an event participant. During my 2 years of working at Generation Entrepreneur, I learned everything that I now know about business and leadership, also meeting some of the best people in my life along the way.

Now as I leave Generation Entrepreneur, I wanted to spend some time reflecting on my experiences, and remember what this organisation means to me.

2018: Leaving My Bubble

How it started

I first crossed paths with Generation Entrepreneur 3 years ago, when I participated in one of their events as a high school student.

It was January 2018, and it was the summer holiday before my last year of high school began. My friend Hannah, who was working at Generation Entrepreneur at the time, reached out to me to participate in their flagship holiday hackathon, Initiate 48.

In the hackathon, you form a team with other high school students, work on a start-up idea for 2 and a half days with mentorship from local founders. At the end, you pitch your idea to investors and audiences.

My immediate answer was “no”. As a high school student in his own bubble, spending almost 3 whole days in a foreign environment, working on a business idea with random people, only to have to pitch it in front of a big crowd sounded like a terrible experience to me. I was rather very much ready to spend that time going to the beach with friends or playing video games in my room instead.

Besides, I had no idea what entrepreneurship was even about — I was never interested in business, and I had never taken any business-related courses in school before either.

Conversation between Hannah and myself back in 2018. By “non free days”, I probably meant my regular gaming hours.

But my friend Hannah kept insisting me to go. (after being on the other side, I wonder if they were perhaps just under the quota for ticket sales?)

Thankfully, she had finally succeeded in convincing me. I was still very reluctant, but those 3 days had completely changed how I view the world, and how I defined success in life from there on.

Through the hackathon, I was in a team with 4 other students to work on the problem of accessibility issues for wheelchair users, especially in their own homes. We developed the prototype, visited hospitals to interview clinicians and patients, and delivered our pitch to judges and audiences.

My first hackathon!

But the biggest thing I took away from that weekend wasn’t to do with business building — it was a mindset change. It was the first time in my life where someone told me to my face that the only dependent variable of your success is your own actions. Hearing it from successful industry mentors who treated and challenged me like a real founder really hit differently.

As a high school student who has lived in a safe bubble his whole life, the common excuse of “bad teachers” or “I’m too young” or “I’m not talented” excused all the dissatisfactions I had in my world. This weekend changed that I learned to take initiatives to solve problems in my community instead of just complaining about them, and realised how trivial and invalid any of my excuses were.

When I came back to school, I was beyond excited. I started running projects to solve the small problems I used to complain about in my community. Some of them included outside-class-hours academic support sessions, raising money to refurbish school environments and gathering student surveys to provide feedback for the school cafeteria.

But more than anything, I wanted to recreate the experience I had at Initiate 48 for all of my friends.

Meeting the team

After I participated in the Initiate 48 hackathon, I actually applied to join the Generation Entrepreneur team and I got rejected. This was fair enough — I only wrote 1 sentence in each of the application questions with questionable quality. There wasn’t a particular reason why, I just didn’t know better at the time.

My infamous first application — for reference, they recommended 1250 characters for each question. I hope this highlights how far Generation Entrepreneur has taken me from where I was originally

But perhaps this lack of… awareness for basic things at the time wasn’t all bad — because it also meant I wasn’t afraid to ask for things.

Whenever I experience something nice, my first tendency is to want to share it with my friends. It was the same with Initiate 48 — I wanted to bring the event closer to home where it was more easily visible and accessible by school students.

This is when I reached out to the managing director at the time, Jack, about an idea I had developed for an event that I wanted to collaborate with Generation Entrepreneur on. Few questions were asked, but the overall response was very positive.

In hindsight, I am so surprised that the team agreed to run an event with me after that horrible application.

And after a couple of meetings to flesh out the idea and figure out the operations, we launched and ran “Challenger” in that April — the first-of-its-kind inter school entrepreneurship competition hosted by my old high school. Special thanks to Jack, Sunnie, Karen, Hannah and the rest of the Generation Entrepreneur team for helping make this dream of mine come true!

Finalised concept for the event.

The event ended up involving over 50 students from 7 different schools, and was everything and more that I envisioned it to be at the time. The Generation Entrepreneur team led the operational and marketing planning for the event, while I worked to push student sign-ups and was responsible for managing the school venue, since the event was over a school holiday period.

One of the workshops at Challenger presented by the managing director Jack.

Being a core part of delivering something of this scale was something I have never done before, and it got me excited to pursue a mission — to help as many students take ownership of their own education and future as possible through spreading an entrepreneurial mindset.

But besides the event itself, what I loved the most about this experience was getting to work with the Generation Entrepreneur team — they were enthusiastic, optimistic and passionate about the work. They were a group of high school and university students who simply wanted to create an exciting learning environment that they wish they had for everyone else.

Generation Entrepreneur team and I after Challenger’s pitch night!

And luckily for me, the feeling seemed to be mutual. After I had finished high school at the end of 2018, I was offered to submit an application to join the team (which I wrote with great care this time) and I officially joined the Generation Entrepreneur team at the beginning of 2019.

All of this happened because I decided to leave my comfort zone and try something new. If you are someone early in your career and not sure what you want to do with yourself, I highly recommend taking action and just start trying new things — you never know how far it will take you.

2019: On The Rocket Ship

The Schools team

The team that I joined was the Schools team, which had just formed at the start of 2019. In the previous year, Generation Entrepreneur started to see a need for our programs from high school teachers, who were also passionate about preparing their students for future of work with an entrepreneurial mindset. From Generation Entrepreneur’s perspective, this was an excellent opportunity to distribute our impact on a larger scale.

I was beyond excited to join this team — I had always been interested in the education industry, and getting to work in that space for a cause I’m so passionate about made the Schools team the ideal team for me.

The role of the Schools team involved:

  • Developing our flagship 1-day entrepreneurship workshop “Startup 101” that is self-contained, and tailored for high school environments.
  • Marketing, selling and delivering the 1-day workshops, iterating from our student & teacher feedback to ensure we are providing the best experiences that we can.
  • Building relationships and the organisation’s reputation as the thought leader in the education space by networking and partnering with teachers and members of the state’s Department of Education.

Like the rest of the organisation, the Schools team were entirely made up of high school and university students. Our team may not be of qualified teachers or have years of business experience, but we worked hard, were customer-obsessed and knew how to motivate the students — and that’s all it took to make this team successful.

This taught me that imposter syndrome is just a sign of guilt — a realisation that you haven’t worked hard enough for a goal that you desire.

Schools team at the start of 2019!

Embarking on the mission

The year started slow as we were still trying to define the optimal process for doing things. Customer acquisitions were difficult, individual workshops took a lot of human resources to execute on and our product still had many rooms for improvement.

But as we kept repeating the process, and focusing our efforts into making incremental improvements upon each iteration, we became very good at what we did after a few months.

Creation of a dedicated schools program section on our website allowed the teachers in need to reach out to us rather than us reaching out to them which made the sales cycle a lot shorter. As our team became more experienced, the operations of running a program was no longer a challenge. Our content had become optimised, no longer warranting huge changes after each iteration.

My first event of 2019 with Hoxton Park High School at Muru-D.

Our break-through point came when we secured a partnership with the state’s Department of Education towards the last quarter of calendar year 2019. The Department offered to sponsor schools that weren’t able to access our programs due to geographical or financial barriers, allowing us to work with 9 very different schools for the rest of that year.

This was another eye-opening experience for me. Getting to work with students and teachers across such diverse demographics helped me broaden my perspectives and gain a cross-sectional understanding behind the current situation and problems in the Australian education space as a whole. We remember how high school was back when we were students, but one would be surprised to find out just how different the circumstances are in the different types of schools even in the same city.

From our 2019 impact report. 19 of these were from our schools programs!

Overall, 2019 was a very successful first year for the Schools team. That year, Schools team alone achieved the following:

  • 19 school programs run.
  • 3 schools outside Sydney impacted.
  • 968 students gone through the program.

Even with the ambitious targets we had in mind at the beginning of the year, we had overshot our goals.

Personal challenges

Like working in any other start-ups, Generation Entrepreneur allowed me to wear many different hats throughout the year.

The first role I had in the Schools team was to be a Volunteer Manager, building a process and infrastructure to recruit and train our new volunteers to help in our events. Then I started to take a bigger role in our schools workshops, first learning to present in the workshops and eventually leading the operations for entire programs. I also got many opportunities to learn and try sales. In one of our recruitment rounds, I even had a go at running the social media marketing campaign.

Presenting a workshop at Birrong Girls High School.

But as someone without much experience doing this kind of work, there were many challenges along the way. The biggest thing for me was dealing with your own failures, learning from them and not letting them bring you down.

I used to be someone who took themselves a bit too seriously, and when you are working in an environment where you are constantly trying things for the first time under pressure, mistakes are bound to be made.

As I was trying the different roles and picking up those skills, I made all sorts of mistakes you could imagine — from having a mind-blank during a presentation, accidentally sending half-written emails to teachers and messing up a few sales calls. Once, I even temporarily took down the company’s website!

At first, these mistakes made me feel terrible. Even with an understanding that the negative emotion doesn’t help the situation and that I should be focusing on what’s next, I couldn’t help but find myself dwelling on those mistakes.

But what’s important is to take the responsibilities for your own failures, reflect and authentically answer the question: “Did I really do everything that I could?” If the answer is no, there is nothing to stress about — if it’s yes, then what were those things and how will I keep myself accountable to implement them the next time? It took a lot of practice and support from others to “get good at failing”, understanding that those failures are already in the past and everyone makes them from time to time.

There were many things that I learned during my first year at Generation Entrepreneur, but knowing how to deal with your own failures and controlling your emotions is the one which I’ll take with me everywhere I go.

Schools team brunch towards the end of 2019!

As I reflect on myself in 2019 at Generation Entrepreneur, I think this is one of the times in my life where I went through the most steep learning curve, both in personal and professional ways. This is also one of those times where I feel like I have genuinely tried my best with no regrets.

But none of this would have been possible without the amazing team that mentored and supported me through the entire year. I am forever grateful for the whole Generation Entrepreneur team, especially for Sunny, Ethan and Jack for facilitating my growth and bringing out the best version of me.

2020: Year Of Resilience

New year, new role

The two co-directors of the Schools team, Sunny and Ethan, left the team at the end of 2019. I was lucky enough to be invited to fill that role in 2020, along with Marina, who had the COO role for the company in 2019. I was very excited — we were coming off the strong foot from the success of 2019, we had a team that we were very confident in, and Marina was probably the best co-director I could have asked for. The two of us spent Dec 2019 and Jan 2020 planning what the year would look like.

One of our priorities was to continue to scale our impact through the flagship Startup 101 program. In 2019, we started to see an operational limit to scale our product. At the end of the day, the program still demanded a lot of our team members to be physically present to execute, which meant our potential impact only linearly scaled with the number of team members we had. This was something we wanted to change.

After long chats with our team and the teachers that we worked with, we decided the first few changes we wanted to try out were to:

  • Identify the parts of our program where students struggle the most (i.e. where they require the most attention from our team members) and make that as easy as possible.
  • Leverage technology to automate parts of the program.
  • Optimise the training cycle for our team to help run the program.

Another ambition of ours was to run a state-wide inter-school competition. Many teachers and parents are still sceptical of the idea of entrepreneurship for high school students. It isn’t taken seriously by many as they would for course works or more established extra-curricular activities, such as debating, music and sports. The question we wanted to answer was: “How can we prove to the world that entrepreneurship education for high school students is something that is so fundamental and important?”

Our response to this was to run a state-wide entrepreneurship competition, backed by a well-known corporate sponsor. We drew a lot of inspiration from the FIRST Robotics Competition, an international high school robotics competition. Marina and Jack from our team had first-hand experience of being guest judges of the competition, and they had been riveted by the amount of passion, energy and school pride that the students and teachers brought into the competition ever since.

After crystallising these goals, we spent the next two months hustling on these ideas with our team. There were lots of struggles, especially in securing a sponsor and hitting the 10 teams sign-up goal for the inter-school competition and building the new 1-day program that was ready to help us scale significantly better. It was all hands on deck, and for me it was always being on emails and phone calls to sign up as many schools as we could. By the middle of March, our efforts had paid off. For the inter-school competition, we had hit the minimum number of sign ups we needed months ahead of the actual competition itself, secured the sponsor to fully fund the competition as well as financially supporting some schools for entry. For our new 1-day program, we had finished building the new program we were proud of and secured almost 10 schools to run the program with already.

But less than a week ahead of running our first workshop with the new program and less than 3 months away from the inter-school competition we had so long dreamed of, we had to make the call to indefinitely postpone all of this. COVID-19 had reached Sydney.

Navigating through the pandemic

COVID-19 made 2020 exceptionally challenging for everyone. For us in Sydney, the virus had started to spread in the community around early-middle of March. Although official lockdowns were not in place yet, we decided to make the call for ourselves to put the safety of our team, students and teachers first. It was a very tough decision to make at the time, but in hindsight I’m glad to say that we made the right choice.

I still remember calling our team that night to inform them that the leadership team had collectively decided to indefinitely pause our current projects that were so close to coming to fruition.

This had a big emotional hit for me personally, as I’m sure it did for everyone else on the team. We had worked so hard, yet everything that we worked on over the first quarter of the calendar year now seemed meaningless.

There was one very obvious and easy option, which was to call it quits until situations got better. The company didn’t have long-term financial commitments and for everyone, this was a part time role that we didn’t rely on for our income so it was a very feasible option to just wait the pandemic out.

But instead, we decided to keep trying — we pivoted to focus on content strategy to keep our teachers engaged, while starting to work on an online program which our team had never done before.

Thankfully, it wasn’t long before a teacher approached us to collaborate on building an online program together for her students. School was done remotely during this time, and she wanted her students to have a 6-week long project-based learning opportunity from home. Even though the teacher knew we had never done an online program for a school before, she had worked with us in the past and she trusted our team and our brand, which we were very grateful for. At that point, Marina and I knew this was one of the best opportunities we were gonna get to break into the online programs space.

But we had a very tight deadline — the program was due to start in the middle of May, and that meant we had less than 2 months to build a great online program from scratch with 6 weeks worth of content. It was all hands on deck again, and we had to push ourselves even harder than we did before to get this program up and running. All of us were way out of our comfort zone when it came to building an online course — there were technical, operational and compliance issues that we had to consider which we have never dealt with before.

Even after the program was built, running the program itself was another challenge. Our whole team was busy marking the students’ work on weekends, moderating the online forums during the week and putting off fires whenever little technical errors popped up. We even had to stretch the program 2 weeks longer due to an unseen clash with the students’ exam period as the school was accommodating for their own challenges.

Despite everything, all of the hard work paid off. Our online program was able to match the student satisfaction and learning outcome levels of our usual in-person program for over 70 students!

From our program case study!

You might have noticed the lack of images in this section. That is because most of the first 6 months in 2020 had gone by with a lot of hard work, but not much direct impact for our students and teachers. Things were getting cancelled last minute when there were new virus breakouts and there were no tangible impacts despite all the work we were putting in — it was only at the end of this program we finally started making impact since the pandemic hit our city.

But there is always light at the end of the tunnel. The next 6 months got a lot better. At the end of June, we inducted 3 new interns to our team, who brought so much energy and passion to the team that it helped everyone feel like it’s a fresh start. We were more used to and better at running online programs, and from August, we had enough control over the virus to start running in person programs again!

My last 1-day program at Concord High School in November.

By the end of 2020, our team had:

  • Worked with 8 schools.
  • Serviced 1 school outside Sydney.
  • 367 students impacted.

When you compare these numbers to the ones we had at the end of 2019, we have definitely taken a step back in 2020. Looking back, we didn’t achieve the initial 2 goals we set out to achieve — the inter-school competition and the restructured program for scale. But when I think about all the challenges we had to overcome, I’m more than proud of what we were able to achieve.

Online programs were something that we had always been curious about, but never had the time and courage to explore it when there were healthy demands of in-person programs. We have explored and discovered so many things that will help guide our future decisions about where we want to take this organisation.

After all, this is still 8 more schools and 367 more students than we would have impacted if we decided to do nothing in the face of adversity.

Thank you, team

Even if it wasn’t for COVID-19, Marina and I both had a big challenge to overcome, and that was learning to lead a team. Both of us were very much the “get things done” type, and neither of us had much experience facilitating a team before. Towards the start of the year, it was very clear that we were outside our elements and didn’t know how to cultivate a great team culture, facilitate authentic 1-on-1 chats or how to delegate and support the team with projects.

Add on top of that, all of the struggles we had from COVID-19, there were times where I felt like I was letting the team down as deals and events were getting cancelled last second everywhere. But our team never gave up, and that meant I couldn’t give up continuing to work on myself to facilitate a great environment for them either. Everyone had their own personal challenges to deal with outside the organisation, and I will always remember and be thankful for the level of resilience our team showed through the year.

Again, Generation Entrepreneur has proven to me that hard work does always pay off. We all hear generic and cheesy advice about being a leader, but when it comes to putting them in practice, you realise it’s another one of those things that you can only be good at over time with experience. To anyone just starting out to improve their leadership skills, here is what I would share:

Always seek objective feedback from others about your leadership style and never stop working on them. Understand every individual member in your team, their story and why they are here. And understand that your role is to take care of your team and the majority of your time should go to actually doing the work with them, then it’s their role to focus on the product and customers. But most importantly, be patient — like any other skill, you will slowly improve with time.

Now, I am happy to say that we have achieved a world-class team culture, jealous of no other!

Team dinner at the end of 2020!

After going through all the craziness together this year, I think this was the only team I could have ever done it with. To Marina, Sam, Ivy, Casey, Marisa, Georgia, Ezra and Fay — thank you for your time, dedication and friendship. I learned so much from every one of you, and know that we will continue to stay in touch in the future!


2020 was my last year with Generation Entrepreneur — that was the best choice for me and the organisation given the circumstances. However, I have this feeling left that I have learned and taken a lot more from this organisation than I have yet given back. I will continue to stay in touch and contribute to the community whenever possible in the future.

To any young students who are struggling to find their passion, my suggestion would be to just start trying things — I never thought a non-for-profit that teaches entrepreneurship to high school students would become something I call my passion and the team my family, but it happened. I hope this story gives you the courage to go out there and try new things. Like the famous quote, the biggest risk you can take is to take no risks.

My story with Generation Entrepreneur ends here, but I look forward to seeing them continue to achieve amazing things in 2021!



Blake Im

Data Analyst & Analytics Engineer. Writing about all things tech and personal reflections.