Tortoise and Hare Software

05/08/2026

Most custom GPTs do not fail because the idea is bad.

They fail because the knowledge behind them is too messy for the GPT to use well.

A lot of B2B technology teams are experimenting with GPTs for sales enablement, content creation, internal workflows, and marketing operations.

But then the outputs come back inconsistent.

The GPT misses context.
It gives generic answers.
It overlooks important details.

The issue is often not the model.

It is the structure of the source knowledge.

GPTs do not retrieve knowledge as full documents. They retrieve it in chunks.

That means a large wall of text is harder for the GPT to search, interpret, and apply correctly.

Structured knowledge documents work better because they give the GPT clearer paths to the right information.

Markdown headings.
JSON fields.
XML structure.
Clear sections.
Field-specific instructions.

Think of structure like an index.

It helps the GPT find the right information faster and produce a better answer.

If you want better GPT outputs, do not just upload more information.

Structure the information better.

The same principle applies to marketing systems.

Unstructured inputs create inconsistent outputs. Structured systems make ex*****on easier to guide, improve, and scale.

That is one of the ideas behind the PRESTO marketing system.

It gives B2B technology companies a clearer structure for turning buyer pain, positioning, search intent, and conversion strategy into marketing that supports pipeline.

If you want to learn more about PRESTO or how structured systems can improve your marketing workflows, reach out to Tortoise and Hare Software today.

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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.

05/07/2026

It sounds simple, but buyer pain points are what underpin the PRESTO framework. The P stands for Pain. People buy for a variety of reasons but when it comes to search engines pain points are among the top.

The more clearly you understand your buyers pain points and what is really motivating them to take action, the better chance you have of attracting attention and earning a lead. You have to establish that you understand their pain point or their purpose for visiting immediately in a compelling hook.

Learn more in the clip below.

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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.

05/05/2026

Most MSPs get compliance completely wrong. They treat it like a product. They overcomplicate it. Or they try to charge a premium for something they can’t clearly define. In this episode, Tim Golden (Founder and CEO of Compliance Scorecard) breaks down what compliance actually is - and how MSPs should be using it. → Why compliance is a process, not a tool → How to position yourself as a facilitator, not just a fixer → The simple framework for delivering compliance without complexity → How compliance uncovers gaps that turn into real revenue This isn’t about adding another service. It’s about changing how you think about value, risk, and your role in the client relationship. If you’re trying to move upstream, get a seat at the table, and stop being seen as “just IT” - this is the shift. Looking for Tim's FTC Safeguards CaaS Facilitation Workflow Document (mentioned in the episode) ? Get it here. It's a practical playbook to help Managed Service Providers (MSPs) guide small and midsize businesses through the legal requirements of the FTC Safeguards Rule (16 CFR 314.4). _____________________________________________________ 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 . .

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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 get compliance completely wrong. They treat it like a product. They overcomplicate it. Or they try to charge a premium for something they can’t clearly define. In this episode, Tim Golden (Founder and CEO of Compliance Scorecard) breaks down what compliance actually is - and how MSPs sho...

05/05/2026

A lot of popular marketing theory is based on consumer marketing which is more impulse driven and quick. B2B lead gen requires a different approach and that's one of the reasons we developed the PREESTO framework. B2B purchases do have an emotional component and an impulse driven component. But overall they are more rational and consideration driven processes. We built the PRESTO framework to support that. Learn more in the clip below from our recent webinar.




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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.

05/04/2026

Too often we spread ourselves to thin by "branching out" to other cities or trying to take clients throughout the state. In this episode, I break down the value of thinking local and how to best attract local buyers to your MSP. Need help with this? Visit https://campers.msp-camp.com/

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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.

04/28/2026

There's still time to register for our upcoming webinar on Thursday.

In this webinar well break down our PRESTO marketing framework that we use to create high quality marketing content and talk about how we are integrating it with AI to increase the quality of marketing outputs and enable our customer's success.8

d8b7ae37-1562-47f5-9a0d-84a51643155d@6f9b629a-489e-4d75-af8b-83f5b4980300?utm_source=facebook&utm_medium=organic&utm_campaign=publer+company+page" rel="ugc" target="_blank">https://events.teams.microsoft.com/event/d8b7ae37-1562-47f5-9a0d-84a51643155d@6f9b629a-489e-4d75-af8b-83f5b4980300?utm_source=facebook&utm_medium=organic&utm_campaign=publer+company+page

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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.

Microsoft Virtual Events Powered by Teams

04/27/2026

In this episode, Brian Gillette talks with Omar Armenteros, CEO and founder of Virtuworks, about the future of managed services and how SaaS is changing the game. With over 30 years in the industry, Omar shares how his company shifted from traditional break-fix models to software-driven solutions that scale and automate to meet today’s demands. They discuss how this change is reshaping the way MSPs operate, why automation is essential for growth, and how customer expectations are evolving. Omar also explains why the traditional MSP model is fading, making way for a new, software-centric approach to IT services. In this episode, you’ll learn: How Virtuworks adopted SaaS to improve operations The importance of meeting changing customer expectations in 2026 Why automation is crucial for growing an MSP business How to adapt to the shift from service to software Listen in to hear how the managed services landscape is evolving, and why embracing software might be the key to staying ahead. _____________________________________________________ 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 . .

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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, Brian Gillette talks with Omar Armenteros, CEO and founder of Virtuworks, about the future of managed services and how SaaS is changing the game. With over 30 years in the industry, Omar shares how his company shifted from traditional break-fix models to software-driven solutions th...

04/24/2026

Register for our upcoming webinar on AI enabled marketing for MSPs. Featuring the PRESTO framework. Next thursday 4/30 12PM Mountain Time.

d8b7ae37-1562-47f5-9a0d-84a51643155d@6f9b629a-489e-4d75-af8b-83f5b4980300?utm_source=facebook&utm_medium=organic&utm_campaign=publer+company+page" rel="ugc" target="_blank">https://events.teams.microsoft.com/event/d8b7ae37-1562-47f5-9a0d-84a51643155d@6f9b629a-489e-4d75-af8b-83f5b4980300?utm_source=facebook&utm_medium=organic&utm_campaign=publer+company+page

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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.

04/23/2026

Traditional search engines have a single query with a single set of results. Generative search engines will run multiple queries in the background before synthesizing a response. It's a deteministic past and a probabalistic future. Learn more in the clip below.




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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.

04/20/2026

I feel like I've been offered the red pill and I took it. Claude Code + N8N is a true game changer for marketing (and business operations). Both are an incredible combination for your MSP to dominate. In this episode we discuss:Why we finally drank the Kool aidWhat we've built recentlyHow to monetize AI and why it's an easy sell I hope this episode is helpful because we have a lot more coming where that came from. Want to join the "AI Show and Tell" with your peers? Start an MSP Camp Trial at: https://campers.msp-camp.com/

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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.

04/20/2026

SEO is a 6 month process and not because of time taken to do the work - but for Google to crawl index and rank pages. Learn more in the clip below.




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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.