Tortoise and Hare Software

Tortoise and Hare Software

Share

Episode 43 - The Cyber Insurance Shield: De-risking Your MSP (w/Guest: Andy Runyan) | The MSP Sales Podcast 05/26/2026

If you are like me you hate talking about insurance. You do not like the checkboxes. You do not like the technicalities. You certainly do not like the liability. For a long time it felt like cyber insurance providers were just looking to make the MSP the scapegoat. But the market has matured. In Episode 43 of The MSP Sales Podcast Brian sits down with Andy Runyan from UKON Insurance to break down the real relationship between MSPs, cyber liability, and security sales. Andy explains why hiding from the insurance conversation is actually increasing your E&O risk. He also explains why playing the "cowboy consultant" and giving unlicensed advice is even worse. Instead of avoiding the topic smart MSPs are using insurance requirements to force the hand on security controls and they are turning local agents into massive referral engines. We cover: → Why you should never ignore cyber insurance (and why you can't fill out the application for them) → The real reason claims got denied during the ransomware explosion → Why "sub-limits" are leaving your clients massively underinsured → The critical difference between cyber warranties and cyber insurance → How to use tabletop exercises to sell Incident Response (IR) planning → Why local insurance agents are the ultimate untapped referral source If you want to stop getting stuck in the crossfire of liability and actually use compliance to drive revenue this episode is for you. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com Learn more about Andy Runyan on LinkedIn Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format! It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values. Get it now at Amazon.com https://a.co/d/hJKoFxg . .

************************

Tortoise and Hare partners with mid-market MSPs to help them increase lead volume, scale revenues, and make their businesses more attractive to prospective buyers when it comes time to sell.

Our marketing team tackles late-stage marketing problems that mid-market challengers face like multi-channel advertising campaigns, SEO, conversion rate optimization, performance reporting, and more.

Apply for a free MSP marketing consultation today.

Episode 43 - The Cyber Insurance Shield: De-risking Your MSP (w/Guest: Andy Runyan) | The MSP Sales Podcast If you are like me you hate talking about insurance. You do not like the checkboxes. You do not like the technicalities. You certainly do not like the liability. For a long time it felt like cyber insurance providers were just looking to make the MSP the scapegoat. But the market has matured. In Epi...

05/25/2026

Still one of my favorite interviews to date, so we're doing a throwback. Enjoy!

************************

Tortoise and Hare partners with mid-market MSPs to help them increase lead volume, scale revenues, and make their businesses more attractive to prospective buyers when it comes time to sell.

Our marketing team tackles late-stage marketing problems that mid-market challengers face like multi-channel advertising campaigns, SEO, conversion rate optimization, performance reporting, and more.

Apply for a free MSP marketing consultation today.

creators.spotify.com

Episode 42 - Stop Acting Like Spam: An MSP Guide to Cold Email (w/Guest: Brian Kelly) | The MSP Sales Podcast 05/19/2026

Most MSPs think cold email stopped working. The reality? Most outbound campaigns fail before anyone even reads the message. In this episode, Brian Kelly breaks down why deliverability has become the real bottleneck in MSP marketing, and why most providers are still approaching outbound the wrong way. Brian shares how he applied a technical, engineering mindset to sales and built systems focused on one core principle: “The best way to avoid being treated like spam is to stop acting like spam.” We cover: → Why most MSP emails never reach the inbox → The real impact of AI on outbound marketing → The role of context, timing, and relevance in outbound → How MSPs are doing the right things in the wrong order If your outbound strategy feels inconsistent, overcomplicated, or ineffective, this episode will challenge a lot of assumptions. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com Learn more about Brian Kelly's services at https://www.automatedmsp.com/ Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format! It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values. Get it now at Amazon.com https://a.co/d/hJKoFxg . .

************************

Tortoise and Hare partners with mid-market MSPs to help them increase lead volume, scale revenues, and make their businesses more attractive to prospective buyers when it comes time to sell.

Our marketing team tackles late-stage marketing problems that mid-market challengers face like multi-channel advertising campaigns, SEO, conversion rate optimization, performance reporting, and more.

Apply for a free MSP marketing consultation today.

Episode 42 - Stop Acting Like Spam: An MSP Guide to Cold Email (w/Guest: Brian Kelly) | The MSP Sales Podcast Most MSPs think cold email stopped working. The reality? Most outbound campaigns fail before anyone even reads the message. In this episode, Brian Kelly breaks down why deliverability has become the real bottleneck in MSP marketing, and why most providers are still approaching outbound the wrong way...

Want your business to be the top-listed Advertising & Marketing Company in Denver?
Click here to claim your Sponsored Listing.

Telephone

Address

Denver, CO

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm