The technology decisions that keep founders up at night

Here's something nobody tells you when you start a company: you'll spend an absurd amount of mental energy worrying about technology decisions you don't fully understand.

It's 2 AM. You're staring at the ceiling. And instead of dreaming about product-market fit or that big client you're chasing, you're wondering if your IT vendor is ripping you off. Or whether that "enterprise-grade" software you just signed a three-year contract for is actually enterprise-grade. Or if your entire customer database is one phishing email away from ending up on the dark web.

If this sounds familiar, you're not alone. And honestly? These anxieties aren't irrational. They're the natural consequence of being responsible for decisions in a domain where you're not an expert — but where the stakes couldn't be higher.

The weight of technology decisions

Let's be honest about what we're dealing with here.

Technology decisions aren't like choosing office furniture. They're foundational. They affect how your team works, how your customers experience your product, how secure your business is, and — increasingly — whether you can compete at all.

The challenge? Most founders and CEOs aren't technologists. You might be a brilliant operator, salesperson, or industry expert. But that doesn't mean you can evaluate whether Kubernetes is overkill for your infrastructure or whether your developer's estimate of "six weeks" is reasonable.

This knowledge gap creates anxiety. And that anxiety is completely valid.

Anxiety #1: "Am I spending too much on technology?"

This one hits hard, especially for bootstrapped founders watching every dollar.

You look at your monthly software subscriptions and wonder: Do we really need all of this? That $15,000/month AWS bill — is that normal? Your competitor seems to be doing fine with a fraction of the tech stack. What gives?

Here's some perspective: Technology spending varies wildly by business model, growth stage, and strategic priorities. A company investing heavily in automation might spend more upfront but dramatically less on labor over time. A company that skimps on infrastructure might save money today and face a catastrophic outage tomorrow.

What actually helps: Benchmark your spending against similar companies (industry, size, growth stage). Ask your vendors for case studies showing what comparable customers spend. And most importantly — tie every technology expense to a business outcome. If you can't articulate why you're paying for something, that's a red flag.

Anxiety #2: "Am I spending too little and falling behind?"

The flip side of the budget anxiety coin.

You read about competitors implementing AI-powered everything. Your industry peers are talking about digital transformation initiatives with seven-figure budgets. Meanwhile, you're running your business on spreadsheets and a prayer.

Here's some perspective: Technology FOMO is real, and vendors exploit it ruthlessly. Not every shiny new tool is necessary. Not every "digital transformation" initiative delivers ROI. Many companies that trumpet their tech investments are quietly struggling with implementation failures.

What actually helps: Focus on problems, not solutions. What's actually slowing your business down? What's causing customer complaints? What's creating operational bottlenecks? Start there — not with whatever technology trend is dominating LinkedIn this week.

Anxiety #3: "How do I know if my IT person/vendor is any good?"

This might be the most insidious anxiety of all.

You've hired someone (or contracted with a company) to handle your technology. They seem confident. They use a lot of jargon. They tell you things are going well. But you have absolutely no way to verify any of it.

Are they actually competent? Are they keeping up with best practices? Are they telling you what you need to hear or what they want you to hear?

Here's some perspective: This is a principal-agent problem, and it exists in every field where you hire experts. You can't fully evaluate your accountant's work either, or your lawyer's. The difference is that technology failures tend to be more visible and more catastrophic.

What actually helps:

• Get second opinions. Periodically have an outside expert review your technology setup. Think of it like a home inspection.
• Ask for explanations, not just updates. A good technologist should be able to explain decisions in terms you understand.
• Look at outcomes. Are systems reliable? Are projects delivered on time? Are costs predictable? These are proxies for competence.
• Check references. For vendors especially — talk to their other clients. Not the ones they suggest. Find your own.

Anxiety #4: "What if we build the wrong thing?"

You've committed to a major technology project. A new system, a custom application, a platform migration. It's expensive. It's disruptive. And you're haunted by the question: What if this is the wrong choice?

Here's some perspective: Most technology projects don't fail because of technical decisions. They fail because of unclear requirements, changing priorities, poor communication, and unrealistic timelines. The "wrong thing" is usually less about picking the wrong technology and more about building something that doesn't match actual business needs.

What actually helps:

• Start small. Prove concepts before committing to full implementations.
• Involve end users early. The people who'll actually use the system should have input from day one.
• Build in checkpoints. Regular reviews where you can course-correct — or kill the project if necessary.
• Accept imperfection. No technology choice is permanent. Most can be changed later, even if it's painful.

Anxiety #5: "What if we get hacked or lose data?"

This one keeps everyone up at night — and for good reason.

Ransomware attacks on small businesses are up dramatically. Data breaches make headlines daily. And the consequences range from embarrassing to existential.

Here's some perspective: Perfect security doesn't exist. Even the most sophisticated organizations get breached. The goal isn't to be unhackable — it's to be a harder target than the next company, and to be able to recover when (not if) something goes wrong.

What actually helps:

The basics matter more than fancy tools. Get those right first.

Anxiety #6: "Why does everything take so long and cost so much?"

Ah, the eternal question.

That "simple" feature request turns into a three-month project. The "quick" system upgrade requires a complete redesign. The budget you approved somehow doubled by the time the project finished.

Here's some perspective: Technology work is genuinely hard to estimate. Software is complex, requirements change, unexpected issues emerge. This isn't unique to your team or vendor — it's endemic to the industry. Studies consistently show that software projects run over budget and schedule more often than not.

What actually helps:

• Add contingency. Whatever timeline or budget you're given, add 30-50%. Plan for the realistic case, not the optimistic one.
• Scope ruthlessly. The single biggest cause of overruns is scope creep. Decide what's essential and protect that boundary.
• Ask about assumptions. When you get an estimate, ask: "What would make this take twice as long?" The answer reveals hidden risks.
• Consider opportunity cost. Sometimes the "expensive" solution that's done in two months beats the "cheap" solution that takes eight months.

The fundamental challenge

All of these anxieties share a common root: you're making decisions in a domain where you lack expertise.

This isn't a character flaw. It's just reality. You can't be an expert in everything, and your job as a founder or CEO isn't to be the best technologist — it's to make good decisions about technology despite not being one.

That's a different skill entirely.

Building confidence in technology decisions

So how do you get better at this? A few strategies:

Develop your technology literacy. You don't need to code. But you should understand basic concepts — cloud vs. on-premise, APIs, databases, security fundamentals. Enough to ask informed questions and detect obvious nonsense.

Build a network of trusted advisors. Find people with technical expertise who can serve as sounding boards. Not vendors trying to sell you something. Not employees who report to you. Independent voices who can give you honest assessments.

Focus on outcomes, not implementations. You might not understand how a system works, but you can absolutely evaluate whether it works. Define success criteria upfront. Measure against them. Hold people accountable for results.

Embrace transparency. Create an environment where your technical team can tell you bad news early. The worst technology disasters happen when problems are hidden until they become catastrophic.

Document decisions. Write down why you made major technology choices. When you revisit them later — and you will — you'll have context. This also forces clarity in the moment.

When to get help

There's a point where DIY technology management becomes counterproductive.

If you're spending more time worrying about technology than running your business, that's a signal. If you've had multiple technology failures or budget overruns, that's a signal. If you're making decisions based on anxiety rather than strategy, that's definitely a signal.

Options range from fractional CTO services to technology advisory boards to strategic consulting engagements. The right choice depends on your specific situation — but doing nothing and hoping for the best is rarely the answer.

The goal: technology as enabler

Here's what good looks like:

Technology that works reliably. Costs that are predictable and justified. Projects that deliver value on reasonable timelines. Security that lets you sleep at night. And most importantly — the confidence that you're making informed decisions, even in a domain where you're not an expert.

That's not an impossible standard. It just requires acknowledging the challenge, building the right support structures, and being honest about what you don't know.

The anxieties won't disappear entirely. Technology will always involve uncertainty and risk. But they can become manageable — background concerns rather than 2 AM ceiling-staring material.

And that's worth pursuing.

Entvas Editorial Team

Helping businesses make informed decisions