WIN

Len DiCostanzo Has Been Building Winning MSP Event Strategies for Over 40 Years. Tune In!

Ian Richardson

Send us a text

If you're heading to Pax8 Beyond—or any major MSP channel event—this episode is your tactical prep guide.

Channel legend Len DiCostanzo joins host Carrie Richardson to share strategic insights from his 40+ years in the IT channel, including leadership roles at Autotask, Kaseya, and Datto. Now leading the coaching and consulting practice at MSP Toolkit, Len helps vendors and MSPs alike improve their partner programs and sales performance—and in this conversation, he breaks down what it really takes to make an event worth the investment.

You’ll learn:

  • The top mistakes vendors make when exhibiting at trade shows
  • What to do instead of hiding behind your booth table
  • How to evaluate your event ROI—and what metrics actually matter
  • Why relationships, not branding, drive long-term value
  • Tips for making every handshake, hallway chat, and happy hour count

Whether you're a first-time sponsor or a seasoned exhibitor, this episode delivers real-world advice to help you turn event spend into sales results.

Find Fox & Crow Group at booth 929 at Pax 8 Beyond.  

Read the blog post inspired by the interview here.


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.

People on this episode