Hire them for buying Salesforce

Sometimes, boring is beautiful.

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A few weeks ago, I published "Fire them for buying Salesforce," which resonated with many of you. I stand by that piece—but like any good contrarian, I also enjoy challenging my own thinking. So, in this post, I’ll explore the counterview: there are times when the "boring" choice is exactly what your startup needs.

You Can Only Afford So Many Risks

Startups operate with limited resources—not just money but attention, cognitive bandwidth, and organizational capacity for volatility. Every risky bet you place consumes these resources, and they don't replenish quickly.

Your startup can only afford to take existential risks on things directly tied to your core value proposition. Everything else should be as boring and predictable as possible.

When Stripe was revolutionizing payments infrastructure, they weren't also experimenting with novel accounting systems. When Airbnb was disrupting hospitality, they weren't simultaneously reinventing how to run A/B tests or manage payroll.

Each unconventional choice creates friction. Each custom tool requires maintenance. Each "different" approach demands explanation to new team members. These costs compound, and suddenly, your team is spending more time managing internal complexity than delivering customer value.

The Opportunity Cost of Reinvention

Time is the scarcest resource in a startup. When you're racing against runway, every hour spent configuring a custom tool, debugging an experimental framework, or training the team on a novel process is an hour not spent on product development, customer acquisition, or fundraising.

Consider two startups:

1. Startup A chooses to build their own CRM because Salesforce is "too enterprise"

2. Startup B buys Salesforce, configures it in a day (complains about it every day after), and moves on

Six months later, Startup A is still maintaining their buggy, feature-poor CRM while Startup B has been fully focused on their actual product. Who's more likely to succeed?

When "Nobody Gets Fired" Becomes Wisdom

The "nobody gets fired for buying IBM" mentality isn't always wrong. It's actually a compressed form of organizational wisdom that recognizes:

1. Predictability has value

2. Setup costs are real

3. Maintenance creates drag

4. Cognitive overhead matters

When you choose established tools in non-core areas, you're not being unimaginative—you're being strategically conventional. You're deliberately limiting your exposure to unnecessary risk.

The Right Time for Boring Choices

So when should you embrace the "boring" option? Here's my framework:

1. For anything that isn't your core differentiator: You're a fintech startup? Experiment with payment processing, not email delivery.

2. When speed to implementation matters more than perfect fit: Sometimes having a working solution today beats having an optimal solution next quarter.

3. For tools used by teams without engineering capacity: Your marketing team needs tools they can use without engineering support.

4. When integration with other systems is critical: Standard tools usually have standard APIs and established integration patterns.

5. When hiring experienced talent is part of your strategy: Familiar tools mean faster onboarding and broader talent pools.

Real-World Examples of Strategic Conventionality

Let's look at some successful startups that deliberately chose boring options in specific areas:

• Figma built on WebGL (innovative) but used standard cloud infrastructure.

• Notion created a novel product but relies on conventional marketing automation tools.

• Shopify revolutionized e-commerce but uses a standard accounting system.

These companies understood that innovation should be focused, not scattered.

The Anti-Anti-Startup Mindset

The truly startup-friendly mindset isn't about reflexively rejecting enterprise solutions—it's about making deliberate choices about where to innovate and where to conform.

A sophisticated startup leader asks:

1. Is this area strategic to our competitive advantage?

2. Do we have the bandwidth to manage custom solutions here?

3. Will the flexibility benefits outweigh the implementation and maintenance costs?

4. Could our resources be better deployed elsewhere?

Sometimes, the answer is "Yes, let's build something custom." But often, it's "No, let's buy the boring option and focus our creativity where it matters."

Knowing When to Be Different

The key insight: Being different everywhere makes you different nowhere. If everything is special, nothing is.

Strategic conventionality means deliberately choosing where NOT to innovate so you can focus your innovative energy where it counts.

This isn't about avoiding risks—it's about concentrating risks where they have the highest potential payoff.

The Path Forward

So, should you fire people for buying Salesforce? Sometimes, yes. But sometimes, you should promote them for recognizing that certain problems have already been solved well enough, and your startup's scarce resources are better spent elsewhere.

The next time someone suggests a conventional solution, don't dismiss it out of hand. Ask yourself: Is this an area where we need to be different? Or is this somewhere we can afford—or even benefit from—being boring?

Because sometimes, the most radical choice a startup can make is to be selectively conventional.