Changing The Game

Charlie Caruso’s background is less of a story about finding a passion and working on it and more of a constellation, where each passion shines on its own and leans into the others into a complex yet fascinating network.

These passions include writing, podcasting, consulting for start-ups, blockchain, NGOs, all of which are tied to her love of problem solving and disruptive technological solutions that puts her in ever new and exciting projects.

Charlie’s trajectory was marked by her constant reliving of a moment that is somewhat rare for most entrepreneurs: The moment when you fall in love with a new idea. Which is what makes her such an amazing guest for today’s Changing the Game episode.

From a very early age, Charlie was the type of kid who would read lots of books and probe adults for logic gaps with question after question, that’s right, a nerd, but not like most of the nerds you saw at high school or maybe in the mirror.

She was the type of nerd that had a very clear talent, one that teachers didn’t seem to recognise at first.

“ A Writer?” they would say, “With those grades why settle for being a writer?”, and yet, it felt right for Charlie, so much so that she saw writing as the way to convince her sister to let her borrow her clothes through a five page contract.

This was when her mother told her she should be a lawyer, and now, a self-published author and a master of international law, Charlie is living proof that the greatest pleasure in life is to do what others say you cannot do.

Like most things in her life, Charlie’s entrepreneurial and podcasting journey began as the solution to a problem, namely being stuck in traffic with nothing good to listen on the radio.

The usual music radio was playing Rihanna’s “S&M”, not exactly what the children in the backseat ought to be listening, switching radios only proved equally disheartening as the alternative, TalkBack Radio was about a Cricketers wife losing pregnancy weight.

Something had to be done. And Charlie was going to take matters into her own hands.

So, after a quick search, she embarked on a journey that would eventually lead her to having her own online radio and podcast long before those were a thing.

This was not an easy journey by any means. From a technological standpoint, Charlie was too early, and circumstances soon began to poke holes at her business model, meaning she had to make too many compromises, ultimately leading to its end.

And yet, there is something of value to be taken from this “failure”, as she did at the time, which is having the fortitude to roll with the punches of having a business sink and going for something new.

In many ways, having a business that didn’t work out was paradoxically essential for Charlie’s success, as her problem-solving mind was able to soon detect the patterns of those mistakes in other businesses, making her an excellent consultant.

Granted, the corporate world was not her natural habitat, but it did have something she needed at the time: money. And it was not long before she found something to be passionate about as a consultant.

She soon found out that helping founders tell their stories and raise funding was something she could really get behind, so much so that she began to undercharge for the sake of sticking with the founders she believed in.

Charlie’s newest project, Quokka Capital is an early-stage venture capital limited partnership created to provide start-ups in Perth with tax incentives in order to help them start off on the right foot and develop.

Quokka operates off a government incentive that gives investors an exemption of tax for investments up to 250 million dollars per investment, a golden opportunity for a state like WA that they want to take advantage of.

This advantage is put to the benefits of founders who are front and centre in reaching their true potential and to expand from WA to the rest of the world.

As of the time of this writing, Quokka has just gotten into its first year, but know Charlie it will not be long before it becomes another of WA’s many success stories.

The one key term that we can get from Charlie Caruso’s story is “problem solving”, which ties directly to entrepreneurship and innovation to the point they can be compared to the sunlight that nurtures a flower.

Every invention, every business, every idea that changes the game is born out of a creative individual’s disposition to meet a need that up until that point had not been recognized, much less addressed.

So with Charlie’s enthusiasm for problem solving, let us get into our thought exercise for the day: What is a persistent problem in your life for which no one seems to have a decent answer? What would you do to solve it?

And if you enjoyed Charlie’s talk and are excited to see more game changers from WA, feel free to check out the changing the game podcast, either on YouTube or on your preferred platform.

Reading Kylie Frazer’s bio may get you a slew of interesting information, including her amazing work at Flying Fox, the venture capital agency she co-founded that helps Australian startups hit it big abroad and interest in bringing empathy to early stage investment.

What you don’t get from her bio is the “uncool” confession that Kylie also loves being a lawyer and that even while practicing law, she was trying to humanise client/firm relations in terms of making the exchange rewarding for both sides.

As we’ll see, this is a pattern for Kylie, one that she perpetrates with good humor and a genuine passion for seeing the founders she funds succeed.

And, as we get to know her, we’ll learn quite a bit about angel investing from her perspective.

“I wasn’t looking for a female partner, I was looking for the best partner”, Kylie remarked about coming together with Rachel Newman for co-founding the Flying Fox, a sentiment that now extended to her yet undisclosed third partner who was confirmed to be a female.

Kylie made a point, however, to remark how women were still shamefully missing from decision making spaces, both in investing and beyond, and that unfortunately, companies like hers were still a minority in the market.

Her views on such matters are worth taking note, as they show what can happen when we let problematic thought patterns get in the way of good intentions.

This becomes clear in her comment on how investors would always hand her female founders to work with based on nothing but her gender, with the underlying premisse that she, as a woman, would only invest in other women.

Getting a woman’s profile on the table solely because they’re female is just as much of a mistake as not doing it for the same reason. Inclusivity is about different people working together in unison, not in enclosed bubbles.

Being an angel investor, Kylie had the chance to work on several trailblazing projects, and though she refused to tell me her favorite one for professional reasons, we still got to hear about the startup that was turning worms into money for the environment.

The company was called “Go Terra”, and it had several contracts in Australia for waste management which they tended to by adding an organic factor into the process: Worms.

Nature’s little janitors are employed to have their fill of food and organic waste and wound up having so much food that they would eventually die of gluttony, but worry not, they had a happy and fitting end as the chubby ingredients in pet food products.

The founder for Goterra, Olympia Jager, eventually got the Australian of the Year Award for her company’s work, showing not only what founders are capable of, but also the potential of companies like Flying Fox, that help them get off the ground.

Something else that’s unique about Flying Fox is its policy regarding sharing their carry with founders, something so unique that it gets to the point of being mindblowing in terms of what it means for the sector.

The initiative arose out of Kylie and Rachel’s desire to walk the talk when it came to being “founder friendly", and to create an environment where founders could help each other while still being rewarded for their efforts.

Sure, most venture partnerships are based off founders mutually supporting each other because that’s just how it tends to work in early stage investments, but being a good lawyer, Kylie wanted their intent to be represented in their structure.

This makes Flying Fox the first company of its kind in Australia, one that hopefully starts a trend of less greedy investment partnerships and funds.

The first thing an investor should bring to the table for their founder according to Kylie Frazer?

Cash.

Sure, you can be a great advisor for founders and bring in great intelligence, but a founder will only know where to put you in comparison to other investors if they know how much you’re bringing in.

Angels are also essential for downstream capital investment strategies, that is to say, helping founders find more long term regular investment, which may come from anywhere in the world and helping them access these investments.

A large part of fulfilling this task is related to aid founders in their decision making in order to position them for earning these investments from abroad through proper long term strategies.

It’s hard not to smile while chatting with Kylie, not just because of her upbeat and welcoming personality, but she speaks as someone that’s had years of experience in angel and early stage investing and constantly uses them to break the glass ceiling.

Kylie’s fun, but she’s also got both feet firmly in the earth while her eyes are set in the future, and both of these are essential characteristics of a good investor and driver of innovation.

And the best part? She does this for the sake of a more human investing landscape.

So, for today’s thought exercise, I'd like to propose the following question: How can you make your business or sector more empathetic? In what ways has it failed to be so?

And if you want to learn more about angel investing and early stage entrepreneurship, remember to check the other episodes of Changing the Game, as we have several interviews with members of Perth Angels and other groups.

2022 was a busy year and I was lucky enough to finish it off with a conversation with Aprill Allen.

Aprill is the COO and co-founder of Tractor Ventures, an initiative focused on providing technology start-ups from Australia and New Zealand with non-dilutive strategic funding in order to foster their growth.

Along with her business and life partner, Matt Allen, Aprill boasts an investment portfolio of over 50 companies and provides her process improvement expertise to the companies supported by Tractor ventures.

Stepping out of the confines of her bio, Aprill tells us how she met her husband Matt while working for the Australian telecommunications company One.Tel in the late 90’s. She would eventually leave the company to become a solo consultant before joining Tractor full time.

Tractor has a “Fridays off” policy which Aprill uses to work on her art studio and can often be found painting on Fridays in between enjoying her weekend with her husband and two teenage sons.

Not having gone through any graduation in the field of technology beyond a computing certificate from the Computer Power Training Institute, which landed her the position in One.Tel from which she’d build the rest of her expertise through experience.

She also points out how much of what she’s learned from her current line of work came from absorbing the information that she was able to catch from observing her husband’s work as a start-up builder.

Aprill’s story is just another trail blazer open to divert from the beaten path of high school-> college -> career along with so many that we have seen on the podcast thus far. It bears repeating that there are many ways to educate a professional. College is just one of them.

So, what’s with Tractor Ventures and “non-dilutive” funding solutions for tech businesses?

Aprill explains:

“We help tech founders who traditionally aren’t super attracted to venture capital, they may not have the same aspirations, they still have ambition but don’t necessarily want to go at that rocketship pace.”

And this is the centre of tractor ventures' entire identity, most ventures try to be rocketships, they tend to be very expensive to build and tend to involve a lot of risks. Sure, there might be a big pay off if they stick to landing, but they also explode just as often.

Now tractors have the distinct advantage of being cheaper, simpler, and easier to fix, a farmer can rely safely on his tractor with the certainty that it will in all likelihood, never explode.

What tractor ventures does is support “tractor” businesses with revenue-based finance within a non-dilutive model, that is a loan that goes back to the fund through a top line share of the monthly revenue.

Tractor Ventures still supports their tech companies with everything they need, much like angel investors would, not only about their gross charges, but also with useful connections through the Tractor Ventures “village” where founders can get in touch and cooperate.

The story of tractor ventures goes back to the year of 2012 when Zero did their dual listing on an IPO on the Australian and New Zealand stock exchanges which paved the way for Aprill and her husband to start a self-made superfund.

Since then Aprill has advised some of the most successful vanguard companies out there, with Flowork being a worthy mention on her part, along Mr.Yum and GoTerra, helping entrepreneurs manage talents at their disposal within the company.

As Aprill told me of all the companies she has worked with, I couldn’t help but notice a glitter of excitement in her eyes when talking about how these businesses have grown, this kind of passion that is quite common amongst angel investors.

The first fact about angel investing is that it tends to be very high risk, and for Aprill and Matt, who were putting in family savings on their investments, while still having to manage things as a married couple.

At first, not coming from a start-up background herself, Aprill told me how she mostly relied on her husband’s experience and “good read of a team’s ability to execute”.

That being said, they are quite different in terms of “risk appetite”, with him being more of a risk taker, whereas Aprill “wouldn’t get upset with you if you described me as conservative”, even if Matt’s more adventurous disposition has rubbed off on her over the years.

Normally, their journey towards investing in a business would start, in Aprill’s words, with Matt getting excited with a new venture, then coming home to make a second pitch to her before they decided to go ahead with the loan.

These loans tend to be no bigger than 10 to 20 thousand dollars, somewhat modest in investing terms which dispels the myth that you have to be rich in order to be an investor, and which are normally balanced with other expenditures such as mortgage.

When questioned about what she and Matt are looking for in their next founder, Aprill already had the answer at the tip of her tongue:

“We’re looking for tech-enabled businesses that are making a monthly recurring revenue of at least 15 grand, and that has a history of growth over the last months, and a healthy runway of 5 to 6 months.”

That being said, Aprill and Matt have not been making as much angel investments as in the past beyond “a couple of follow-on things”, with most of their investments being made on Side-Stage, a new fund set up by Matt and some partners which launched last year.

According to Aprill, women in the investing world have begun to become more aware of each other and are beginning to expand their networks to include other women, something that has come with a growing conscience of who they are within that space.

However, she points out how despite these advancements, the investing sector is still far away from being anything close to diverse, which is to be expected as the sources of these problems are structural and engraved in culture.

“It has to do with women not having senior roles” she explains “boardroom roles, seat level roles, anywhere near as man do”, which means that when these women get within Aprill’s age spectrum, they lack the money to even think about investing.

Fixing this issue is going to demand a restructuring of these systems through policy and government intervention, as women investors themselves can only go so far to remedy these injustices.

My talk with Aprill did a great service to angel investing by dispelling the traditional view we have of an investor (black suit, top hat, money bags falling out of their pockets), and brought it closer to home. Literally.

When you talk to Aprill Allen, you have the impression that, while she certainly is an interesting person, she’s also the type of person you could meet in your neighbourhood.

She discusses the risks of investment with her husband, worries about mortgage, all the while raising two teenage sons, a far cry from the “sharks” we hear so much about. That is, she’s living proof that anyone can become an investor.

With that in mind, it’s time for today’s thought exercise: if you were going to get into investing today, what field would you pick and why?

Also, don’t forget to check my website and YouTube channel for more conversations like the one you read above.

Terry Rich is a successful CEO and President of 25 years who loves to engage and entertain audiences across the globe.

During his appointment by three Governors, his leadership increased lottery sales and profits by 50%. He also led the Blank Park Zoo to profitability from a $600,000 deficit while positioning it as the second largest attended attraction in the state. But his national insight on business, banking, gaming, TV production, marketing and PR led him to success in his professional career and to his passion for public speaking. Oh, and he’s also given away over $1 billion.

Recently, Terry headed the team that cracked the largest lottery fraud in US history. During the investigation, Terry oversaw day-to-day operations while considering longterm consequences, adapting quickly to change, and delivering on promises.

Before that, he started four successful entrepreneurial businesses, and has numerous national media appearances including ABC, NBC, HBO, CBS, 20/20, CNN, CNBC, USA Today and The New York Times; a movie host on Starz!; and appeared as a panel guest on the "Tonight Show".

He’s a disruptive innovator and entrepreneur with a drive for integrity and honesty. He’s worked in the trenches, survived new business trends and had success with generational changes. Terry’s keynotes are energetic, motivating and perfect for an early morning, lunch or after dinner presentation.

Terry Rich has authored two books: The $80 Billion Gamble and Dare to Dream, Dare to Act.

Cheryl Mack is a connector.

She takes pleasure in bringing people together and driving them towards genuine connections within the communities she creates, be them big or small.

With a description like that it would be natural to assume she helps businesses with community building with the end of creating harmonious work environments, but that is not where the surprises stop.

Today we are going to do a deep dive into Cheryl’s work at Aussie Angels, her journey towards becoming the amazing professional she is, and how she is changing the game for the Australian market today.

Check it out:

Cheryl finding her calling in helping people connect was a natural development from her natural inclinations as an extrovert.

Cheryl graduated in business with a major in marketing, but if you asked her, she’d tell you that the biggest takeaways from college were less about social media strategies and more about how to reach out and “work with difficult people”.

Soon after graduating and cutting her teeth as a team member at freelancer.com, she went on to found “StartCon”, where she got to put founders and investors in the same room for the very first time.

There was, however, a slight problem, a simple, yet nonetheless hard to solve issue where “If you put over one thousand people in the same room expecting them to make the right connections, that isn’t really going to work out.”

And so, Cheryl began to figure out how to facilitate these matches made in heaven by herself.

In doing so, she brought to the forefront of her brand a fact that is often neglected, especially when on the subject of investments: that they care about people and work with the same dynamics other human relationships work.

Cheryl’s way with people has been instrumental in her role as an angel investor, after all, Investments are all about people talking, sharing ideas and getting into ventures together.

And according to her that made all the difference in the world.

Now, she’s relatively new to angel investing, and some people have even (however timidly) pointed out that she was rather divergent from the mental picture most people have of an angel investor.

On the other hand, that hasn’t really stopped her from going into this space with everything she has, to the point where she could eventually own up to a portfolio of over ten companies.

Connections also played a large role in this aspect, as Cheryl was able to help her founders not only through financial support, but also in helping new start-ups reach out to other investors and manage their interpersonal relations on an in-house level.

At the end of the day, more than anything she learned in classes, it was Cheryl’s ability to see investing as a team effort and coordinate it as such that made her successful in what she does today.

Now, if you were paying attention to the intro for this episode of Changing the Game, you might remember me mentioning how Cheryl is the founder of Aussie Angels, an initiative which she described in the following words:

“Aussie Angels is a place where angels can co-invest in the most seamless and fun way possible.”

What sets this group apart from the rest is how it allows angels to follow other investors whom they like and share their own ventures. They can also join a syndicate without a minimum investment and work under a lead investor.

Lead investors are the people looking for new companies, making deals and explaining why they are investing in particular ventures and sharing it with their syndicate who can decide if they’ll join in or not.

It also makes the whole process of forming an angel syndicate that much easier and cheaper, which as someone undertaking that task right now, I can’t thank her enough.

A little-known fact about Australia is that early-stage investment is extremely regulated, with aspirant angels and regular investors alike being required to hold certain amounts in assets and other prerequisites that make investment limited for the general public.

I asked Cheryl, at the risk of making her uncomfortable, what was her first check-size was to gauge what a new investor could expect to spend in the land down under.

Luckily, she was rather understanding and told me, without hesitation, that her first investment as an angel was 10 thousand dollars for two different start-ups.

She made it very clear, however, that this was under half the minimum amount most founders were willing to take, which made it hard for her to begin investing, which is 25 thousand dollars.

On the other hand, having less than that doesn’t mean you’re locked out of angel investing if you are regarded as having a higher value as an investor, it all depends on the needs of the founders.

Cheryl Mack perfectly demonstrates through her story and expertise that before even mentioning anything remotely technical about business, it must first be understood in a human light.

Human relations are at the basis of any conjoined effort, and if neglected, no other aspect of an enterprise can work the way it was supposed to, a fact that can easily become buried under the talk of deadlines, bottom lines and other lines of such.

So, for our mental exercise for today, I’d like you to take a look at your current work relations, are there any tensions getting in the way? Or better yet, is there any way you can make the people you get along with feel like they can rely on you?

As the first half of 2022 closes, a new page in Changing the Game starts as I share a table with a guest for the first time, a moment I had the pleasure of sharing with the amazing Esther Oh.

Describing her background is a little hard since there seems to be very little she hasn’t done.

Esther has several qualifications in fields from IT to law, having worked in the boards and committees of several universities, and having received a ministerial appointment for reforming the TAIFF.

However, what brings Esther to this episode of changing the game is less her extensive list of titles and achievements, and more the story of how she came to add “entrepreneur” to her already prolific resume.

This story, unfortunately, starts with her having to go through a rather traumatic event:

Esther describes herself as a mother who’s had her vision transformed by a series of traumatic experiences, and came to find an answer in technology for the issues that contributed to her tribulations.

Agile 8, is the result of this broadening of vision, a company that combines AI with enhanced virtual reality to empower health professionals with something akin to x-ray vision, allowing them to work smarter, faster, and safer.

Her story is the perfect example of how the hardest blows life deals us often prepare us with the strength to change the game.

“How?” you may ask? By making the commitment of not allowing what happened to us to happen to others.

Empathy can make an innovator out of anyone.

So, what was the traumatic experience that lead to the founding of Agile 8?

Well, let us begin by saying that Esther’s son was a perfectly healthy boy who began to develop some sight issues.

As any mother would, Esther took him to a doctor, the first doctor, who was not aware of the gravity of the illness affecting her son’s eyes, a mistake shared by the second doctor, a mistake which the third doctor affirmed could have been corrected had it been identified earlier.

This was how, while still a child, Esther’s otherwise perfectly healthy son lost his sight permanently.

Esther went through what might be a mother’s worst nightmare, to see her son suffer for the rest of his life due to an issue that could have been avoided were it not for a series of problems that impeded the ability of health professionals to operate at their best capacity.

Firstly there was the knowledge gap that existed between doctors, as neither of the first two specialists, Esther visited had the same knowledge as the last one, which inevitably lead to the delay in treatment that cost her son’s sight.

This is when she realised that the ability of frontline doctors to accurately diagnose an issue as soon as possible not only could have helped her son but could effectively be the difference between life and death for thousands of people.

But where this kind of suffering can enclose many of us in our own struggles, her background as a health professional and entrepreneur allowed Esther to see herself as part of a much larger problem. A problem she could give her best to solve.

And this is exactly how she defined innovation: problem-solving.

To be more specific, Esther defined innovation as problem-solving using through tackling it from different perspectives, that is, to find and try all possible solutions for solving that problem in the most efficient way.

This process starts with a deeper renewal and transformation of your mind. Where other parents could be “wallowing in sorrow and blaming the doctors who didn’t get it right”, Esther took a completely different route.

She saw the severe pressure frontline doctors endured and decided that instead of adding to that the weight of her sorrow, she was going to make their jobs and lives easier through the implementation of technology.

At the end of our talk, the single most important lesson Esther Oh had taught was this: that suffering can enable you to make the world a better place. At the center of our life’s most traumatic experiences are problems that we could help to solve.

When Esther had to watch her son become gradually blind due to a misdiagnosis, she was able to identify the core issues that lead to this tragic turn of events and decided that she could do something about it. And then, she went and did it.

I want you to think about the worst day of your life. I know that is a very uncomfortable request, maybe even an offensive one. But! At the core of that experience may lie the secret to a better world.

The strength to turn the worst experience in your life into a source of good is within you, and today, I invite you to find it.

Royce Crown is what you could call the quintessential entrepreneur, starting his first business at nine when he decided to sell lemonade to the other kids on his street.

Ten years later he was inaugurating his very first food truck, which would come to be the staple of another future business, but not before he got his hands on a license to work as a helicopter pilot, transporting goods from land to yachts in the Mediterranean.

Coming to Australia in 2012, Royce started his new food company, setting up shops in metropolises across the world before going back to his original passion for aviation

Driven by this passion, Royce started his new company, Monarch, which along with his trajectory, was the main topic of a conversation we had on the “Changing The Game” podcast, but just in case you’re in a hurry, here are some of the highlights:

So, how does a person become a helicopter pilot? What are the requirements? That’s exactly what Royce was discussing with his father, who believed that colorblind people could not get a pilot’s license.

It just so happened that Royce had watched a show called Jeopardy that debunked this assertion, so he, as a colorblind young man, decided to strike a bet that if he could pass the eye exam, his father would have to pay for the course.

And, given everything that I’ve disclosed in the introduction to this article, I think you can guess who won that bet in the end.

At first, Royce didn’t think much would come out of this license, but when he was living in the Mediterranean and applying as a deck hand at a mega yacht, it just so happened that he caught ear that they were needing a pilot.

So, remember, no skill gained goes to waste.

Royce’s experience as a pilot made it so that when he came to Australia in 2012, he brought along an idea for a software that would allow pilots across the world to automate their pricing.

The goal is now to take this price automation system and transfer it to usual places people go to in order to survey flight options, thus widening the customer pool for charter flights.

Royce does, remark that charter flights, in general, tend to be more expensive, but that the price tag more than made up for in comfort, speed and security. Not having to trudge through a crowded airport and bump shoulders with strangers is worth a couple of hundred dollars.

In effect, what Monarch does is make the experience of private flights, which is still seen as exclusive to the rich and famous, more accessible, and despite the increase in the overall passage price, cheaper when you look at the value gained.

Effectively, Monarch is another step forward in an industry-wide movement to make charter, or private, flying more accessible to the general public, while also ensuring that pilots can not only cover all operating costs but make a decent profit.

The idea itself is quite fascinating, a world where private flights are not the privilege of the rich and famous, but just another option anyone can opt for while paying a fair price is a real change in the game.

An example given by Royce was a pilot who got paid to take a client and three of his family members from Sydney to the Gold Coast, with the full rate, and still got to transport 12 backpackers on the way back for $135 per seat.

The clients got to fly comfortably on a private plane for a fraction of what one would expect. The pilot managed to cover all expenses on the first flight and got a good deal of extra income on the way back.

Monarch’s system would only make such operations easier by calculating the price of such ventures based on available seats, fuel, distance and so on. Such an innovation could easily change the way we think about commercial flying.

Speaking about the future of his enterprise, Royce expressed quite a bit of enthusiasm:

However, if Australia provided its fair share of opportunities for Monarch, it also brought along its load of challenges as well, with Royce highlighting his company’s difficulty in finding good funding.

He reports being able to raise a certain amount of money through angel groups, but breaking through a conservative investment landscape that is more focused on social good companies has taken over the Australian market.

There’s also the challenge of selling an entirely new concept, which most innovation-focused businesses run into eventually. When it comes to investing, a new idea can take off or crash and burn right on top of you, so most people are comprehensively thorough.

Thinking about how Royce came to where he is at the moment, it’s hard not to recall the butterfly effect, where a small dislocation in the air caused by the insect’s wings can lead to a hurricane.

Likewise, a simple discussion over the dinner table with his father made Royce not only a pilot but a pioneer in the aviation industry that can completely change how we see private flights.

So, as is customary for these articles, I would like to leave you with the following thought exercise: Try to trace back your butterfly moment. That one thing that kickstarted your journey into where it is today.

It might seem like a silly thing, but entrepreneurial life is full of hardship, and being able to nail down the very first moments of your story gives that heroic mental narrative that makes everything worth it.

If you own a technology start-up in Australia, you may have heard the name Greg Riebe, and if you haven’t, you’ll be glad to be doing so right now.

Greg is the winner of the 2020 Australia’s Angel Investor of the year, largely due to his talent for mixing enabling technology with highly scalable business models that are the perfect dream of most investors.

He was the head behind Perth’s first ever technology incubator, managed funds for investing in technology start-ups and has co-founded many successful tech companies himself and today he works advising entrepreneurs on how to become investment ready.

And, while doing all of the above and much more, he still found the time to be on the Changing the Game show to talk about how his work has been leading the charge for innovation in Australia and beyond.

Before he could become the investment titan he is today, Greg was (according to his own words), a “propeller head, a geek” that is, a highly specialised software engineer that worked at SGIO during the early 2000s.

From this position he was moved to manager, getting his first taste for innovation and advisement before leaving SGIO for a non-for-profit which was able to get a license from the Australian Government to run an investment fund for IOT startups.

That was the birth of the very first tech incubator in Perth that we mentioned, which according to Greg also acted as an accelerator, providing capital for new businesses while simultaneously nurturing their growth.

While working in that investment fund, Greg found that his passion was to enable other people’s dreams, to “that little glint in their eyes” become a true flame. Ultimately, that is what made him an angel investor, and such a good one at that.

Now, much like private flights, which we discussed in the last episode, people tend to look at investment as an activity that is exclusive to people who are already rich to begin with, a thought that Greg immediately shot down.

He explained that there are many levels that there are plenty of low-cost investments to be made, especially in stock exchange, and that it all comes down to having the knowledge necessary to “identify, filter, select, structure and manage an investment.”

You also have to take your “appetite” into consideration, or how much you are expecting to earn out of an investment, and what risks you are willing to take to see that investment through.

There is also the option of seeking out managed funds who will look after your investments for you and make all of these decisions under a more specialised context, not to mention the benefit of it being much less time time-consuming.

So, if you were thinking about investing and felt like you had neither the knowledge nor wealth to do it, know that there are options for all wallets and levels of experience, not to mention plenty of risk-free (and often free in general) ways of learning.

At this point we have thrown the term “Angel Investor” quite a lot, but what does it actually mean?

Greg explains that Angel Investors are a collective, or individual that “applies their time, their own money and their knowledge to participate in a venture”, often in the early development stages, sometimes before they even hit the market.

Angel investors will then look at such companies through their network and identify those that represent a real opportunity, and then reach out to collaborate with these promising starting companies to help them grow.

What differentiates Angel Investing from your usual Investment is that you are not only providing financial funds to a business, you are holding classes to teach them necessary skills, or even providing specialised services to nurture that venture’s growth.

Now, this process is not always smooth, and Greg himself described it as “a bit of a rollercoaster”, but he remarks how in these ups and downs, it’s always the quality of the team itself that sees the company through.

At the end of the day, Angel Investors are always investing in people.

A veteran investor like Greg is bound to have some good advice for both people looking for opportunities to invest their money and entrepreneurs that are looking for an angel investor to call their own.

So naturally I had to interrogate him on what were the criteria he used when picking prospects, and his answer, however simple, provides incredibly useful insight:

You may have notice that Greg’s work is majorly focused on tech, and that is not by accident, as his entire background is on software engineering and computers, which means that he has the tools to judge any proposition made by a tech startup.

The same goes for most investors, but Greg also made it clear that you also have the option of leaning on someone else’s knowledge, which is where the idea of investment collectives like Angel groups actually came from.

This, what is known as “Syndicalisation” and it teaches us an important lesson: Investing, and business in general, is all about people.

You could have the most promising enterprise with all the funding in the world, but if there’s no trust between the investor and the CEO, if the team can’t work together without furniture being thrown, the venture is doomed to fail.

On the other hand, if the relationship network between all parties is solid, and built on genuine affinity and unity of purpose, there’s very little that a venture can’t do.

What I loved the most about my conversation with Greg Riebe is that while giving out priceless advice, it also managed to bring some much-needed humanisation to the topic of investments.

Too often investing in a business is seen as just throwing money at a series of letters and numbers expecting to get something return, but in effect, what we are doing is giving someone’s dream a chance.

So, for today’s thought exercise, I would like to hear about the big investment that changed your life. It doesn’t have to be money related. Tell me about that one time someone invested their time, attention, or knowledge on you, and what came out of it.

On the last season of changing the game, we covered the pressing issue of gender diversity and the journey of women who have defied the forces arrayed against them to carve a piece of the cake for themselves.

Now, As the second season of our podcast begins, we are going to be talking about how new ideas from forward-thinking individuals around the world are transforming society before our very eyes.

And what better way to kick things than by interviewing the founder of WeMoney?

So that’s exactly what I did, and you can check out some of the highlights from our conversation below:

Every entrepreneur has a story, and Dan’s started his by talking about her mother, an immigrant who had to raise her children while coming from a very disadvantaged socio-economical background, without having the simple advantage of speaking English.

By watching his mother do everything she could in order to raise him and his siblings, Dan learned a valuable lesson: If you want to make it in this world, you have to hustle.

On the other side, however, Dan’s father made the options at the table very clear from the start, you either pick up a briefcase, or a tool box. Dan chose neither. He had decided that controlling your own destiny was a far better way of living life.

He started to work on the things he truly loved, a plan that hasn’t really changed since he first took it on.

According to Dan himself, he was never the model student, or at least not for the most of his time as a student, mostly because he “didn’t have the attention span to be interested in the formal education system”.

He even recalled how most of his grades would always be either “Satisfactory” (as it was written at the time), or that dreaded “BE” for “below expectations, which would get one of his teachers to taunt him by saying he would “never amount to anything”.

Now, most people would be rightfully angry at such a declaration, especially for someone who was supposed to make sure that didn’t happen, yet Dan decided to take that a step further and graduate at the top of his class out of sheer spite.

As it turns out, a grudge makes for terrific fuel for people’s ambition, and not only did Dan prove his teacher wrong by becoming the best student in his class, he actually scored a spot on a US University to make revenge that much sweeter.

The fact that he had actually come to like the academic process came later as a nice bonus for his dedication.

If you were to search up Dan’s LinkedIn page and read his Bio, as I do with every guest, instead of the usual three-paragraph description, you would only find the words “Dan from WeMoney”. So, what is WeMoney?

In order to understand what any business is about, we need to know the problem it intends to solve, and on this matter, Dan started out by saying that his startup is “a social and economical wellness company.”

He then went on to explain how we have all had a bad experience related to money at one point in our lives, and the main reason for that is that most people, and especially newer generations, think about their finances on a very short-term basis.

Combine that with the overwhelming complexity of our current financial system, which has us making all sorts of complicated decisions based on concepts it don’t fully understand, and it’s no wonder we have a rocky relationship with money.

In order to solve this issue, WeMoney offers an automatisation of personal finance, to put it on “autopilot”, not only in order to avoid future headaches, but also to make it work for you and generate further income.

Something that they call “self-driving money”.

Okay, so that is WeMoney’s mission. But what does it actually do?

Firstly, it allows you to connect over 230 accounts to their platform and have a unified view of all your financial assets, including a monitor track of your credit health that lets you know your credit score and gives you tips on how to improve it and use it.

Secondly, it provides you a community. Have you ever noticed how there’s this unspoken rule that you are not supposed to talk about money with friends and family? How are you supposed to understand finances without talking about it?

Well, with WeMoney you can actually get in contact with people, watch how they are applying their funds and where, learn from them and ask questions in order to better manage your wages.

Lastly, it takes away all the friction of getting the best possible deal and outcome of investments and transactions. That means getting the best home loan and figuring out when to consolidate your superannuation will no longer be a frustrating process of trial and error.

Dan Jovevski could not have been a better guest to kick off season two of Changing the Game, not only because his story hits so close to home for me, as we both take after the extraordinary women who raised us.

Dan is a perfect example of how businesses are grown out of people noticing a necessity and tending to it, not just for their own benefit, but for others as well in providing both a powerful financial tool and a source of education that is sure to change the game.

Now comes the part where I leave you with the first creative exercise of our new season: What is a great need that you have identified in society, and what kind of innovation could you bring to the table in order to solve it?

Not only is Monique Mattos the proud mother of three kids while also being a managing partner and coworker of mine at Visagio, she is also living proof that the two of these things can be perfectly balanced in a single person.

Her main passion is the development of people, and she points to the success of others as the main source of happiness in her life, a drive that comes in handy as Monique advocates for greater inclusion and diversity in her sector.

She is also a fellow Brazilian, which gave us plenty of common ground to discuss all of the topics above in the Changing The Game podcast, where we managed to dig up a series of magnificent insights for people looking to make a real difference in the world.

When discussing the influences that led Monique to become an engineer, she mentioned how one of the main factors towards her decision was her own father, who worked as a logistics manager in a multinational company even though he was not graduated.

Monique greatly admired her father for this and would often stop and listen whenever he talked about his work at home, and when the time to choose her career, there was no sense of “manly” or “girly” professions in her mind.

From this, we can get an important lesson, which is this: Heroes remove barriers that separate the possible and impossible. It’s also not hard to see that when Monique set out to become an example for other women, there was a part of her father in this as well.

That barrier women face in the field of engineering would only start to become clear when she got into college, where the ratio between women and men in the Industrial engineering course was unbalanced to the point where there were eight men for every woman.

Monique describes her trajectory to her prominent position within Visagio as one filled with its bumps and obstacles, the major of which, according to herself, was the bump of being a woman in a male dominated industry like STEM.

She sought to bring the perspective of being the only woman in the room into meetings, projects, deliverables, wherever it could be brought into the forefront for everyone’s attention. A difficult process, but one that proved to be rewarding in the end.

This trait Monique shares with many of the extraordinary women who I’ve interviewed: That she was able to use her adversities to establish herself as an example, blazing the trail for future generations of women in her field.

As is very common in Brazil, Monique partook in many different internships while in college, going through companies such as Michelin (which she didn’t like all that much, and Shell, which provided more of a corporate work environment.

Monique liked working at Shell well enough, but she started wanting to do more, which is when she caught wind of this Company called Visagio which was founded by five engineers and had strong ties to her university.

She applied and got a position there.

While working at Visagio, Monique started getting into consulting and how she could apply everything she had learned at her course while still living the dynamic work life with several clients and projects which she so desired.

If Monique was a minority at her university course, this was not about to change at work either, and in every company she worked for, be it as an intern or consultant, she would only see men in decision-making positions when looking up.

Monique’s drive to change this scenario came less of a desire to see herself o any other woman in a position of power within the company, and more out of the desire to open the gates for all the women that were going to graduate after her and look for jobs in their field.

During her journey in Visagio, Monique decided to come to Australia, pursuing an international experience that could further complement her career. And a project had just come up.

Her husband (or boyfriend at the time) already had some experience that would make the transition easier, and at the first opportunity, the two of them took the plunge together and moved down under.

From a financial standpoint this was a smooth transition, as she was an accomplished professional with a job waiting for her in Australia, but the social and emotional aspect of this change was much worse. After all, she did not know anyone.

Her husband, on the other hand, had it harder on both ends as he had to start from scratch on his new home, but Monique makes a point to highlight how the both of them were only able to work it out because they were partners through the whole process.

Monique used this for an example as to how changing the game is not about setting up a competition between the genders, but rather a cooperation where all parties work together towards a common goal that is better for everyone.

There are many takeaways from my conversation with Monique Mattos which someone with a hunger for change and a fire in the eye for justice and inclusion will be able to pick up from her story.

I’ve learned from Monique that opening a path, when there isn’t one already there, is not only good for the advancement of our own goals, but for the uplifting of anyone that shares in our struggle.

But, maybe more importantly, I’ve learned about the importance of having a role model. Monique had her father, I had my own mother, what about you? Who is the one person you look up to most?

That will be your thought exercise for today.