Jim Smith Proper Sky IT Appears on WIN with Richardson & Richardson

Jim Smith from Proper Sky IT went from the Peace Corp to Entrepreneurship!  Learn more about his amazing journey on the WIN Podcast!

Navigating the turbulent waters of entrepreneurship and cybersecurity requires a captain with unwavering determination and a strategic mindset. Jim Smith, the visionary behind Proper Sky, embodies these qualities and more.

In the recent episode of the WIN podcast with Richardson & Richardson, he shares his compelling narrative that starts with his transformative experience in the Peace Corps, leading to the helm of a successful Managed Service Provider (MSP).

The Ups and Downs of Business Growth with Jim Smith

Jim's journey is marked by peaks and valleys, with each trough teaching a lesson in resilience and each crest demonstrating the fruits of perseverance. Starting a business is akin to sailing in unpredictable seas; the loss of a major client can be like a storm that tests the sturdiest of ships. Jim recalls the gut-wrenching reality of downsizing, his commitment to never laying off good employees, and the crucial role of seeking external advice.

His life-changing encounters at IT Nation and his participation in the Goldman Sachs 10,000 Small Businesses Program serve as beacons guiding other entrepreneurs through similar straits.

The growth of a business is a voyage in itself, and Jim shares insights from the early days when his MSP resembled a "pirate ship of IT."

The transition from a one-client reliance to a diversified client portfolio is a lesson in risk management.

Jim emphasizes the importance of transferring sales knowledge to new team members, fostering a company culture that's both innovative and structured.

As we sail further into the conversation, cybersecurity emerges as a paramount concern.

Jim highlights the lurking dangers that businesses face in the digital age. Proactive measures like Endpoint Detection and Response (EDR) become not just tools, but essential armor against ransomware attacks.

Jim advocates for using cybersecurity as a strategic marketing tool, providing reassurance to clients and creating a competitive edge.

What's Next for Jim Smith and Proper Sky?

Peering into the future, Jim considers the potential impact of industry regulations and the proactive role that MSPs like Proper Sky play in safeguarding against cyber risks.

He offers a glimpse into the evolving landscape where AI will shape offensive and defensive strategies, and MSPs will need to humanize technology in preparation for the challenges ahead.

Jim Smith's voyage is not merely a story to be told; it's a compilation of wisdom for the modern entrepreneur. It's a reminder that while the seas of business and cybersecurity may be unforgiving, with the right crew, knowledge, and resilience, success is not just a destination—it's a journey.