Tortoise and Hare Software

06/02/2026

Are you building a sales process or just avoiding doing the hard work? A lot of MSP owners are stuck trying to build the perfect AI-powered Rube Goldberg machine. They want a system that sells for them. They obsess over tools, CRMs, and complex automations. In this solo episode of The MSP Sales Podcast Brian Gillette breaks down why the exact skills that make you a great engineer are actively killing your sales numbers. He strips away the noise and brings it back to the five foundational questions you must answer before any marketing can work. If nobody is buying your product it is time to sell a different product. We cover: → The 5 fundamental questions every MSP must answer → How to repackage managed services as the foundation for AI adoption → Why you must clarify your positioning before you spend a dime on lead gen If you are tired of overcomplicating your growth and want a straightforward path to closing deals 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 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.

Are you building a sales process or just avoiding doing the hard work? A lot of MSP owners are stuck trying to build the perfect AI-powered Rube Goldberg machine. They want a system that sells for them. They obsess over tools, CRMs, and complex automations. In this solo episode of The MSP Sales Podc...

06/01/2026

In this throwback episode, we revisit the reality of MSP Marketing. No one starts with doing everything! Add one thing to your strategy at a time. Spend time refining and improving and getting an ROI BEFORE you add anything else. In this episode, we lay out actionable strategies to do just that. Ready to supercharge your marketing? Start a trial at: https://campers.msp-camp.com/

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

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.

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.

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...

05/26/2026

In the latest episode of the Aesopians podcast, we sit down with Scott Millar of IT Rockstars Ltd.

Scott gives us his thoughts on generating leads for MSPs via a webinar focused approach that helps "build relationships at scale."

Webinars are a tried and true method for generating demand in B2B and Scott and his team have gone all in on the process of helping MSPs host, promote, and extract value out them to turn digital events into warm sales conversations and pipeline.

Check out the episode on Spotify, YouTube, or Apple podcast, and also check out the recently refreshed IT Rockstars website with pricing and packages for their webinar lead generation service.

https://tortoiseandharesoftware.com/blog/aesopians-e9-webinar-lead-generation-for-msps-ft-scott-millar-of-it-rockstars/?utm_source=facebook&utm_medium=organic&utm_campaign=publer+company+page

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

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.

In this episode we sit down with Scott Millar of IT Rockstars to chat about webinar lead generation for MSPs. Learn more in the podcast.

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.

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.

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...

05/18/2026

Building Alltek was not easy. If I had to restart tomorrow, this is exactly what I would do. Want the cheat code? Visit https://campers.msp-camp.com/ for 50% off for a limited time.

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

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.

05/12/2026

How would you start an MSP in 2026? Most would copy what’s already been done. Same services. Same pricing. Same positioning. That’s the problem. In this solo episode, Brian Gillette breaks down exactly how he’d go from $0 to $1M ARR today - without reinventing the tech, but completely rethinking how it’s packaged and sold. → The 3 core offers I’d build: MSP, AI as a Service, and vCSO → How to sell outcomes (time, growth, productivity) instead of tools → How to reframe managed services as “insurance” (but why you shouldn’t lead with it) → Why most MSP marketing fails - and how to fix it without changing your stack This isn’t about doing more. It’s about saying the right thing, to the right audience, in the right order. If I were starting over today - this would be the playbook. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.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.

How would you start an MSP in 2026? Most would copy what’s already been done. Same services. Same pricing. Same positioning.That’s the problem. In this solo episode, Brian Gillette breaks down exactly how he’d go from $0 to $1M ARR today - without reinventing the tech, but completely rethinkin...

05/11/2026

Get tickets at ScaleCon.com

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

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.

05/11/2026

Your custom GPT is only as good as the examples you give it.

A lot of B2B technology companies build a GPT, add some background context, and expect it to immediately produce strong landing pages, social posts, blogs, or ad copy.

Then the output feels close, but not quite right.

The tone is off.
The structure is inconsistent.
The copy sounds generic.
The examples don't match how your company actually wants to communicate.

That isn't always a GPT problem.

It's usually a training problem.

One of the simplest ways to improve GPT output quality is to give it examples of strong finished work.

Not just instructions.

Examples.

For most formats, one or two manually created examples can make a meaningful difference.

A good MSP server support landing page.
A good network support landing page.
A good cybersecurity service page.
A strong social post.
A strong blog intro.
A strong CTA section.

Those examples teach the GPT what “good” looks like for your company.

Format.
Tone.
Structure.
Level of detail.
Buyer relevance.
How much explanation is enough.

Don't expect your GPT to guess your standards.

Show it your standards.

Start with one or two high-quality examples for each major content type.

Then, as you use the GPT and create better outputs, keep updating the knowledge base with the strongest examples.

That's how the tool gets more useful over time.

This is especially important for MSPs and B2B technology companies because the copy has to do more than sound polished.

It needs to speak to real buyer pain, explain technical services clearly, support search visibility, and help convert serious prospects into conversations.

Generic examples lead to generic output.

Good examples help create copy that is much closer to your actual positioning, offer, and sales motion.

If you're using AI to support your marketing, don't just build prompts.

Build a repeatable system.

Learn more in the clip below and book a free consultation if you want help turning your website, SEO, and content process into a stronger lead generation engine.

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

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.