This blog was originally featured in the September 10th, 2025 newsletter found here: INBOX INSIGHTS, September 10, 2025: You Get What You Pay For, Small Data Breaches
You Really Do Get What You Pay For
Last week, my dog walker spent exactly ten minutes with my dog. She took her outside, gave her quality attention, checked her water, and headed out. The bill? $25.
For a moment, I felt that familiar sticker shock. Twenty-five dollars for ten minutes of work? That math made my brain hurt a little. But then I stepped back and reconsidered what I was actually paying for.
I’m paying for her experience with large breeds who can be… enthusiastic. Georgia is overly enthusiastic at times and 150 lbs of muscle. I’m paying for her background in pet safety and emergency care. I’m paying for the peace of mind that comes from knowing my dog is with someone I trust completely—someone who won’t panic if something goes wrong.
In other words, I’m paying for expertise. And you know what? It’s reassuringly expensive.
The “Reassuringly Expensive” Principle
My business partner Chris has this phrase about sushi being “reassuringly expensive.” When you’re about to eat raw fish, you don’t want the cheapest option on the menu. You want confidence that someone with serious skills prepared your meal, that the ingredients are top-quality, and that the restaurant follows strict safety protocols.
The price tag becomes a reliable signal of quality, care, and expertise.
This principle applies far beyond sushi or pet care. Right now, it’s especially relevant in the world of business consulting and digital transformation. (And trust me, I’ve seen enough transformation projects go sideways to know the difference good expertise makes.)
The AI Expert Explosion (And Why You Should Be Cautious)
Here’s what’s happening in the market right now: Everyone is suddenly an “AI expert.” People who discovered ChatGPT a few months ago are now offering consulting services on artificial intelligence strategy. The market is flooded with inexpensive options and overnight experts.
I get the appeal of a bargain—who doesn’t love saving money? But when you’re making decisions that could transform your entire organization, the discount option carries some serious risk.
What Makes Something Worth the Investment
When I’m evaluating any service or expertise (and I’ve done this more times than I care to count), here’s what justifies a higher investment:
Time and Experience
- Years of trial and error, with real lessons learned from failures
- Pattern recognition that comes from seeing similar challenges across multiple organizations
- The ability to anticipate obstacles before they derail your project (this one’s huge)
Proven Track Record
- Documented results with real companies facing real challenges
- Case studies that demonstrate depth beyond surface-level success stories
- References who will actually pick up the phone and give you honest feedback
Depth of Knowledge
- Understanding of fundamental principles, not just whatever’s trending this month
- Ability to adapt strategies when technology evolves (because it absolutely will)
- Strategic thinking that connects tools to measurable business outcomes
Ongoing Support
- Confidence that your investment will deliver lasting value
- Someone who will tell you honestly what won’t work for your specific situation
- Available guidance when implementation gets complicated (not if, when)
Why Our Course Represents Strategic Value
I’m going to be direct here: our new digital transformation course carries a significant price tag. And frankly, that makes me a little uncomfortable to talk about. But that investment reflects something specific.
We’re not teaching you how to use AI tools—I’m not an AI expert, and I don’t pretend to be. What we’re teaching is how to prepare your organization for digital transformation, whether that involves AI or whatever technology comes down the pipeline next.
This distinction matters because tools change rapidly. I’ve watched countless “revolutionary” technologies come and go. But the fundamentals of process optimization, team dynamics, and organizational change management? Those stay remarkably consistent.
I’ve spent over twenty years working in process optimization, operations, team building, and organizational behavior. I’ve watched companies succeed spectacularly and fail miserably at transformation projects. I’ve made my share of mistakes, learned from them (sometimes the hard way), and developed systems that consistently deliver results.
That experience—those sometimes painful lessons—represents the real value of the investment.
The Reality of True Expertise
Here’s something that genuinely makes me squirm: I really don’t like calling myself an “expert.” The word feels presumptuous, even after two decades doing this work.
But I am confident in my experience. The systems I’ve developed and refined. The patterns I’ve learned to recognize. The mistakes I’ve made and (hopefully) won’t make again. The organizations I’ve successfully helped transform.
This knowledge didn’t just appear overnight. It’s the result of years of focused work, continuous refinement, and plenty of learning moments that weren’t exactly fun at the time.
Your Strategic Evaluation Framework
The next time you’re considering any significant service investment, use this evaluation process (I wish I’d had this checklist years ago):
Assess the True Value
- What exactly am I purchasing? (Skills, experience, peace of mind, or simply a low price?)
- What’s their documented track record with challenges similar to mine?
- How long have they been doing this specific type of work?
- What support do they provide when implementation gets messy?
Questions to Ask Any “Expert”
Before making your decision, ask potential consultants or service providers these specific questions. Their responses will tell you everything you need to know:
Experience and Background
- “Can you walk me through three specific projects similar to mine and the actual results you achieved?”
- “What’s the biggest mistake you’ve made in this type of project, and what did you learn from it?”
- “How long have you been doing this exact type of work?” (Not adjacent work—this specific expertise)
Approach and Methodology
- “What’s your process for projects like mine, and how do you handle unexpected challenges?”
- “Can you provide references from clients who faced similar challenges to ours?”
- “What would you need to learn about our organization before proposing a solution?”
Ongoing Value
- “How do you ensure the changes stick after the project ends?”
- “What ongoing support do you provide during implementation?”
- “What would you tell me if you thought your solution wasn’t right for our situation?”
Pay attention not just to their answers, but to their confidence level, specificity, and willingness to discuss failures and limitations. The best consultants I’ve worked with are refreshingly honest about what didn’t work.
The Bottom Line
Sometimes the most expensive option isn’t the best choice. But often, a higher price reflects genuine value: proven experience, documented results, and the confidence that comes from working with someone who has been doing this work long enough to know what actually works (and what doesn’t).
Your business transformation is too important to entrust to the lowest bidder. Look for the option that’s reassuringly expensive—where the price reflects real value, proven experience, and the peace of mind that comes from working with someone who has the depth to guide you through the inevitable challenges.
The right investment in expertise today can save you significantly more in avoided mistakes, faster implementation, and sustainable results. (And fewer late-night calls wondering why nothing is working the way it’s supposed to.)
What are you willing to invest in experts? Reply to this email or join our free Slack group, Analytics for Marketers.
Interested in learning more about our new AI-Ready Strategist Course? Sign up at trustinsights.ai/aistrategycourse
– Katie Robbert, CEO
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Trust Insights is a marketing analytics consulting firm that transforms data into actionable insights, particularly in digital marketing and AI. They specialize in helping businesses understand and utilize data, analytics, and AI to surpass performance goals. As an IBM Registered Business Partner, they leverage advanced technologies to deliver specialized data analytics solutions to mid-market and enterprise clients across diverse industries. Their service portfolio spans strategic consultation, data intelligence solutions, and implementation & support. Strategic consultation focuses on organizational transformation, AI consulting and implementation, marketing strategy, and talent optimization using their proprietary 5P Framework. Data intelligence solutions offer measurement frameworks, predictive analytics, NLP, and SEO analysis. Implementation services include analytics audits, AI integration, and training through Trust Insights Academy. Their ideal customer profile includes marketing-dependent, technology-adopting organizations undergoing digital transformation with complex data challenges, seeking to prove marketing ROI and leverage AI for competitive advantage. Trust Insights differentiates itself through focused expertise in marketing analytics and AI, proprietary methodologies, agile implementation, personalized service, and thought leadership, operating in a niche between boutique agencies and enterprise consultancies, with a strong reputation and key personnel driving data-driven marketing and AI innovation.
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