What you'll learn from Jon's story
Meet Jon
I'm Jon Leslie, a 55-year-old SaaS executive, entrepreneur, and founder of a remote consulting business called Broad Cove Insights. Reflecting on my journey, I believe that age should never be a barrier to doing your own thing. Throughout my career, I've traveled the globe helping customers, which turned into working remotely, ultimately leading me to start my own consulting business.
What I do for work
I come from the game industry (by way of ERP software if you can believe it). After producing and shipping multiple AAA titles for some of the best studios in the world, I transitioned to a Swedish company called Hansoft. They provide best-in-class project management software to the game and other industries.
This career change led to living as an expat in Sweden and traveling around the world (literally three times during the course of one year), evangelizing, and consulting with Hansoft customers in over 25 countries.
When Hansoft was sold to Perforce, I stayed with the original three Hansoft founders and performed the same role for their new collaboration tool, Favro. This led me to move to San Francisco and a few more trips around the globe.
For three years, I worked remotely in San Francisco, collaborating seamlessly - and mostly asynchronously - with the founders nine time zones away in Sweden.
I moved to Maine in 2016 and have worked remotely ever since, both for Favro and my own company, Broad Cove Insights, providing remote-first, game development, and agile consulting services.
Welcome to my "office"
For me, it's all about flexibility. I don't want to go into too much detail, but I've worked from the beach, pool, or local cafe… you name it. Variety is a big perk of remote work. I've also worked while on "vacation". For example, I recently took a trip with some friends to Baja and worked from Mexico for a week, taking client calls from the resort.
Ironically, during Covid, with the family all at home, I got distracted and needed a dedicated workspace, so I found an office. This wasn't a traditional office—it was my choice, and it was brilliant. I found a group in a similar situation who had leased a conventional office space pre-covid and transformed it into individual offices. I rented a private office with a beautiful corner view of the river, which was surprisingly economical. If you ever want a corner office, go get your own.
Eventually, as my son returned to school full-time, I no longer needed that office, so I let it go. I now work primarily from my home office.
Join me for a day in my life
I don't want to share too much here because there's a fine line between sharing the reality of this kind of lifestyle and bragging. Here in Maine, for example, during summer, I can choose to work less without taking a vacation. It's great to say, "Okay, this time of year, when the weather is nice, I don't want to work too much," and then work more when Maine winter hits and my son's back in school. When school holidays come around, like the long summer break, I reduce my work to take advantage of the weather and spend more time with family. Of course, there are client demands and unavoidable meetings, but the freedom is immense.
Every year, we spend two weeks in Kauai, Hawaii. During that time, I still work, taking meetings, sometimes as early as 4 AM due to the time zone difference. But there's something extraordinary about finishing all your meetings by 7 AM while your family is still asleep. It feels great to have done a day's work in a few early hours, freeing up the rest of the day. Building a life where I don't need to take vacations because my work fits seamlessly into my lifestyle is truly a gift.
How I got started
I started my career after attending Bentley College in Massachusetts, now Bentley University, where I pursued a Computer Information Systems (CIS) degree. This was back in 1987 when Bentley was evolving and introducing more technical majors. My interest in technology stemmed from my early days when I was influenced by my Dad, who worked for Digital Equipment Corporation, one of IBM's main competitors. I was fortunate to have one of the first home PCs, which sparked my fascination with coding before most people even knew what it was.
Straight out of Bentley, I landed a job as a programmer. I was lucky to find a mentor, Maurice Plourde, who convinced me to join a small manufacturing software company instead of one of the big banks. This was pivotal because I wasn't pigeonholed at the small company and learned far more than just my role. I interacted directly with customers and gained hands-on experience in software implementation and product/project management.
As the dot-com era began, my career took a turn. I dived into B2B startups, facing the typical highs and lows, including the eventual failure of one venture. However, this period led me to Tibersoft, where I worked on connecting restaurant suppliers with restaurants digitally. This job involved extensive travel and onsite customer interactions, which was kind of the remote work equivalent before Zoom, and I loved it.
In my early thirties, I decided to quit working for a year and a half and travel. It was a now-or-never type of thing. After a transformative trip around the world, I transitioned from traditional business software to the creative realm of video game development. During my travels, I met an Xbox Microsoft Game Studios producer, who invited me to join them. I ended up working on a launch title for the Xbox 360 - Amped 3. This period was exhilarating yet grueling, teaching me the harsh realities of game development crunch times. At its worst, we worked 16-hour days, seven days a week ahead of launch. Brutal and insane.
After the launch of the Xbox 360, Microsoft decided to exit much of its first-party game development, and Take-Two Interactive acquired our studio. This was another intense experience, and eventually, the studio was closed down in the middle of pre-production for Amped 4. Upsetting, to say the least.
Luckily, I quickly found a job with an indie studio (that promptly became Electronic Arts) as a producer and designer for the Tiger Woods PGA Tour franchise. This role allowed me to work on some cool projects, including the first Nintendo Wii golf game, which introduced a physical golf swing using the Wii controller. Still pretty proud of that one.
From there, I moved to Harmonix, working on the Rock Band series. It was awesome to go from snowboarding to golf to pretending you're in a band with plastic guitars and drums. We were using this software for production called Hansoft. I started talking to the Hansoft founders, three Swedish entrepreneurs and eventually became their product's game industry evangelist.
This role entailed moving to Sweden, which perfectly fit my love for travel. The role became a long-term partnership with Hansoft and later Favro, their cloud-based project management tool. I helped them open their San Francisco office, working remote before remote became more common. After a while, it became clear that the San Francisco office wasn't working out.
So I asked if it would be cool to move to Maine, where my parents had retired and work remotely from there, and the founders said sure. To do this, I rationalized that it was just me in the US and that Maine was 3 hours closer timezone-wise so it actually made more business sense for me to move..
Going out on my own
A year or so after moving to Maine, Favro and I parted ways as employee/employer, and I became a Favro Agile Partner and official provider of Favro training and certifications. That was the birth of Broad Cove Insights. Encouraged by one of Favro's founders, I took the plunge into entrepreneurship. My first client was… you guessed it… Favro, illustrating the strength of professional relationships and networks.
Throughout my career, I've seen the steady paycheck become a trap for many. There's a sort of Stockholm syndrome where people get addicted to the security of a job, even though it was the job that caused their dissatisfaction in the first place. My advice to the younger generation is to minimize reliance on traditional employment and maximize entrepreneurial efforts early in their careers. If you can accept a bit of risk and uncertainty, the learning, freedom, and fulfillment of running your own venture are unparalleled.
Looking back, I realize that starting my own business later in life was daunting, but the experience and connections I accumulated over the years are invaluable. My story underscores that there is always time to pursue your goals and carve out your own path. If you have the opportunity to do your own thing, go for it. You won't regret it.
My message to the world
Reflecting on my journey, I'd like to share one key message with the world: the incredible potential of productizing your knowledge. This idea of moving from selling your time to creating a tangible product based on your expertise is a powerful evolution. Imagine not just sharing your knowledge but transforming it into something that can continually provide value and generate revenue.
Moving forward and envisioning the next step beyond productizing knowledge is creating an actual product: a game, a SaaS, a community, or something similar. It's a progression. It's a systematic transition from being an employee to selling your time, then productizing your knowledge, and eventually using that knowledge to create a digital product. Talking this through, I see it's a more secure way to make this significant shift. Instead of taking a considerable gamble, you build your way up, accumulating experience and capital along the way. Starting your own business offers the best education possible. It's an influx of learning where you must master everything from marketing to sales to accounting.
The sheer amount of learning can be daunting. For some, the idea of so much undiscovered territory is overwhelming, and that's perfectly okay. But the level of freedom and empowerment this knowledge buys you is priceless. If you and I can spread this message—showing people the risks, the safer ways to navigate them, and the immense rewards—we can truly make a difference.
It's important to highlight that this path is more challenging in many ways, but the payoff is much greater.
Yes, start with a job. I believe you need that experience to grow and build your initial professional network. You will learn not only what to do but also what can be done better. Use that as fuel to start your own thing.
Today, it's easy to get stuck in the pattern of job -> dissatisfaction/layoff -> job search -> repeat. It's a mindset where you're almost a prisoner. It seems impossible to break free. I'm obviously a big fan of remote work. If a company offers work location and time flexibility, that's fantastic. But if a company dictates where you need to be and when you need to be there it might be time to break the pattern and bet on yourself.
To everyone out there, understand that while this entrepreneurial path is challenging, it offers unparalleled freedom. The knowledge and experience you gain are invaluable. If you're considering this journey, start by leveraging your current skills and relationships and gradually transition into creating and selling products based on your expertise. This approach minimizes risk and maximizes the potential for success. Remember, starting and running your own business is the most incredible education you can get. It's tough, but the freedom and satisfaction are worth it.
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