Confessions of an IT Business Owner Podcast ConnectBooster

In this episode, IT services-specialized attorney Brad Gross shares his experiences, advice and expertise on technology businesses and liabilities, including cybersecurity concerns, with host Ryan Goodman. From the complexities of protecting your firm’s assets and delivering a dynamic portfolio of managed services to constructing the right contracts and agreements, the duo hit on many legal aspects associated with running an MSP.
Gross discusses the rise of new regulatory and industry compliance measures and other changes being driven by insurance companies and local, state and federal legislation. How will the services you deliver and the data your MSP manages affect your legal and financial liabilities? MSPs must pay attention to the shifting landscape to protect their own businesses.
Properly designed services agreements and contracts can help minimize those risks. How can IT business owners build the right protections into their quotes for new and existing clients? Listen to this insightful episode of Confessions of an IT Business Owner for the answers to those business-critical questions.

In this episode, ConnectWise SVP, International Sales and Strategy Gregg Lalle shares his thoughts on the channel’s future with host Ryan Goodman. From advances in managed services tools to the latest cybersecurity, he discusses how technology changes over the past two decades have affected the IT services business.
Today’s MSPs have to support a multitude of continually changing advancements and support a growing number of business models and infrastructure designs. While IT services firms are flourishing in this “age of technology” and enjoying a plethora of opportunities and solutions options, keeping up with the fast pace of innovation and continually changing clients' needs can be a real challenge.
While dealing with the complexities of innovation and working through issues related to industry consolidation, MSPs still have businesses to manage. How can IT entrepreneurs continue to grow sales and profitability with so many distractions? Tune into this episode of Confessions of an IT Business Owner to find out.

Huntress co-founder and CEO Kyle Hanslovan discusses all things cybersecurity, including why MSPs must take a more active role in defense, with host Ryan Goodman in this information-packed episode. From military recruit to cybersecurity expert and entrepreneur, Hanslovan has the ears of the channel and shares his experiences and insight into one of the most critical technology areas for IT services providers today.
One important theme in this episode is the need for MSPs to drive awareness and tighten down defenses. Hackers and ransomware are not going away, and Hanslovan hits hard on the need for vendor transparency to secure the supply chain. It’s not about having a vulnerability, but the response by everyone in the IT ecosystem.
How can MSPs succeed in those tough cybersecurity conversations with clients? What are the opportunities, myths and realities in this business-critical and profitable space? Check out this episode of Confessions of an IT Business Owner for all the juicy details.

In this riveting new episode, host Ryan Goodman covers a couple of valued topics with Frank DeBenedetto, CEO at Two River Technology Group and Founding Partner & CFO at audIT Sales Presentation System. As an early adopter of monthly recurring revenue, Frank understands the value of the MSPs model and the need for efficient sales processes to maximize profits.
His experience in the financial services industry and a strong focus on cybersecurity are major differentiators for Two River Technology Group. A solid understanding of the compliance and data protection needs of this vertical helps his team land new clients in this space, and those best practices transfer easily to other businesses.
How can IT services professionals strengthen their sales processes and leverage unique expertise to generate new income streams? Check out this episode of Confessions of an IT Business Owner for the lowdown.

TruMethods founder and president Gary Pica discusses the finer points of MSP sales in this informative episode with Connect Booster Executive Vice President, Dan Austin. An expert at building and selling MSPs, Pica now helps his peers reach their full potential as IT business owners.
What motivated him to become a serial entrepreneur and a go-to authority in sales and M&A? Pica shares his thoughts on what it takes to build a million-dollar MSP and provides ideas for generating new revenue streams and boosting profitability. From building a high-power sales team to developing new markets and identifying the best prospects, this conversation covers what it takes to succeed in the managed services arena.
How should MSPs adapt their sales and business practices to maximize MRR and cash flow? Listen to this latest episode of Confessions of an IT Business Owner for all the details.

IT Hall of Famer and Global Technology Distribution Council (GTDC) CEO Frank Vitagliano discusses the growing and rapidly transforming value of IT distribution with host Ryan Goodman. With the continued rise of the cloud and evolving workplaces, MSPs and vendors can benefit greatly from these key industry partnerships
In addition to providing an overview of the health of distribution with consolidation and all the new investments, Frank shares his insight on the latest tools, offerings, and support programs that empower channel partners. Change is the operative word. Distributors are adapting services and business models to align with the changing needs of MSPs, VARs, and vendors.
How can IT services professionals leverage these relationships to scale their offerings and drive new incremental revenue? Check out this episode of Confessions of an IT Business Owner to get all the details.