Send us a text
Jim Smith from Proper Sky IT WINS by Keeping Clients Secure
In this episode of WIN, host Carrie Richardson sits down with Jim Smith, the founder and CEO of Proper Sky, a managed service provider based in Philadelphia.
Episode Highlights
- Jim's Early Entrepreneurial Ventures: Studying entrepreneurial studies at Drexel University and starting a remote pharmacy concept.
- Peace Corps Experience: Managing the largest technical college in the South Pacific and developing a knack for solving problems with limited resources.
- Founding Proper Sky: How a Perl script and Craigslist helped him acquire his first clients, and the growth journey from there.
- Overcoming Major Setbacks: Losing a major client that accounted for 90% of revenue and the subsequent business challenges.
- The Importance of Coaching: The role of external advice and programs like Goldman Sachs' 10,000 Small Businesses in shaping his business acumen.
- Hiring and Building a Team: The significance of his first hires and how they contributed to the company's success.
- Future of Cybersecurity: Predictions on AI's role in cybersecurity and the importance of being prepared for cyber incidents.
- Empathy in Business: The human aspect of dealing with cyber incidents and building trust with clients.
Memorable Quotes
- Jim Smith on Entrepreneurial Resilience: "The longest, most stressful period of my entire life... there's nothing worse than laying off good people that actually are doing the work."
- On the Importance of External Help: "It taught me that it is much better to pay for good advice than it is to do it yourself in a lot of circumstances."
- Future of Cybersecurity: "As AI increases, there's going to be a counterbalance... helping organizations recover and be emotionally ready for the onslaught."
Jim Smith
- Role: Founder and CEO of Proper Sky
- Location: Philadelphia
- Background: Entrepreneurial studies at Drexel University, Peace Corps volunteer, 20+ years in the MSP industry.
- LinkedIn: Jim Smith LinkedIn
Links and Resources Mentioned
- Proper Sky: Website
- Goldman Sachs 10,000 Small Businesses Program: Website
- Adam Grant:
Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?
Serial entrepreneurs, life partners and business partners, they have successfully exited from multiple businesses (IT, call center, real estate, marketing) and they help other business owners create their own versions of success.
Ian is certified in Eagle Center For Leadership Making A Difference, Paterson StratOp, and LifePlan.
Carrie has helped create and execute successful outbound sales strategies for over 1200 technology-focused businesses including MSPs, manufacturers, distributors and SaaS firms.
Learn more at www.foxcrowgroup.com
Book time with Carrie here!
Be a guest on WIN! We host successful entrepreneurs who share advice with other entrepreneurs on how to build, grow or sell a business using examples from their own experience.
