The Luxury of Doing Less

Every week, I see the same problem play out. As an investor, you get handed overly complicated marketing plans and struggle to make sense of them. It feels like a tangled mess of strategies, channels, and projections. I know that feeling because I’ve been there. After reviewing over 50 go-to-market plans in due diligence over the last four years, one truth stands out: there is a luxury in doing less.

Even when I was a CMO, I misunderstood this. I thought complexity meant sophistication. I thought detailed plans and multiple strategies would impress the CEO. But here’s the reality—CEOs don’t want complexity. They want clarity. They want to know there’s a simple, effective system in place that delivers results.

And here’s where it gets worse: Most companies don’t have a clear focus on what actually needs to happen at each stage of ARR. Under $1M? Under $5M? Under $10M? Under $20M? Each stage requires different priorities, yet I see companies trying to build scalable systems before they’ve proven their ability to execute. That’s how businesses get stuck.

So, what happens next? As an investor, you apply pressure. You push for detailed plans. You want to see a roadmap that covers every possible angle. CEOs feel that pressure and pass it down to their go-to-market leaders. The result? Overcomplicated bottom-up and top-down strategies that look impressive on paper but collapse in execution.

And here’s why that doesn’t work. Focus, time, and execution are the most valuable resources in a business. The moment you dilute them with complexity, results suffer. Marketing teams lose confidence because they’re stretched too thin. Execution slows down. Prioritization gets lost. Instead of accelerating growth, companies stall.

Here’s what I would do instead. Simplify the system. I tell companies under $5M or $10M ARR to follow a seven-step approach:

1. Sell and serve 10 customers (or 20-50, depending on your market size). Don’t overcomplicate with inbound, outbound, and multi-channel experiments. Just focus relentlessly on getting those customers.
2. Prove the channel works. What drove those 10 sales? Identify the repeatable process.
3. Upgrade your operating model. Now that you know what works refine it to make it more efficient.
4. Build the scalable line. Once you’ve nailed a repeatable process, layer in people, tools, and processes that support scale.
5. Prove the team can execute. At this stage, build a high-performing team that can consistently deliver results.
6. Scale channels and organizational structure. Once execution is proven, expand into additional channels and grow the team appropriately.
7. Hit your number. By following the steps in order, you hit the next milestone and are ready to repeat the cycle on a larger scale.
8. Repeat process 1-7 for your following revenue milestones.

This Week’s Tangible Prompt for Investors & CEOs

For Investors: One of investors' most significant mistakes is pushing their portfolio companies to scale too soon. You want to see a detailed plan, but you need to understand whether they have clarity on their next milestone. Instead of asking for an exhaustive strategy document, ask these questions:

• Are they clear on their next milestone? It is not the grand vision but the next step they must take.
• Have they demonstrated that they can successfully sell and serve a cohort of customers? If not, why?
• Are they focused on proving what works, or are they trying to do everything simultaneously?

Encourage your CEOs to focus on execution at the right stage. Scaling too soon wastes resources and creates unnecessary complexity that takes years to unwind. Your role as an investor isn’t to push for expansion before the foundations are in place; your role is to ensure companies have the discipline to execute at the right pace.

For CEOs: One of the biggest challenges you face is the pressure to scale. You feel it from investors, the board, and even your team. The result? You overcomplicate the go-to-market strategy. You create too many channels, moving parts, and plans that look great in theory but fail in execution.

Here’s the mindset shift you need: Instead of asking, "How do we scale?" ask, "How do we sell and serve our next 10, 20, or 50 customers?"

• What’s the single most effective channel right now? Instead of optimizing across five or six different channels, focus on the one already working.
• Are you clear on why customers are buying? Is your positioning nailed down, or are you constantly tweaking it without understanding what resonates?
• Are you building your team too early? Too often, I see companies hiring ahead of need instead of proving they can execute with the current team. Focus on proving execution before expanding.

The goal is to remove unnecessary complexity and focus on execution that drives actual results. Investors, push your portfolio CEOs to embrace the luxury of doing less. CEOs resist the temptation to overcomplicate their strategy and double down on what works.