The Hidden Cost of Delegation
What founders give up when they step back too early
Leverage is one of those words that sounds precise but gets used lazily. At some point, it stopped meaning control and started meaning distance. Fewer meetings. Fewer decisions. Less involvement. The business grows, the calendar clears, and somehow things still feel heavier than they should.
Most founders don’t give up leverage intentionally. They give it up incrementally. One hire meant to “free up time.” Another meant to “professionalize.” A third meant to remove friction. None of those choices are wrong on their own. The trouble starts when delegation turns into detachment — especially from the parts of the business that generate money and signal reality.
Hiring is often treated as a reward for success. You’ve earned the right to step back. You’ve put in your time. Now it’s time to work on the business instead of in it. That advice sounds reasonable until you watch a founder lose their feel for customers, pricing, or momentum. The work gets done, but judgment thins out. Decisions start traveling through layers. Context gets lost. By the time something shows up on the dashboard, it’s already old news.
There’s a difference between delegating tasks and delegating understanding. The first is necessary. The second is dangerous. Founders who scale well tend to keep their hands on a few specific levers longer than anyone tells them they should. Revenue conversations. Hiring decisions. The early signs of friction that never make it into a report. They don’t micromanage, but they don’t disappear either.
This becomes most obvious around the first few senior hires. Sales leaders. Ops leaders. Anyone brought in to “own” a function that used to sit squarely with the founder. These roles can extend leverage or quietly hollow it out. The difference usually comes down to why the hire was made. Was it to amplify strength — or to escape discomfort?
Few people are as blunt about this tradeoff as this week’s guest, Eggs! The Podcast guest, Kayvon Kay. His perspective isn’t theoretical. It comes from staying close to revenue even when he doesn’t have to — and understanding what founders lose when they don’t.
Staying Close to the Engine
Kayvon Kay is the founder of The Sales Connection, where he helps companies build and operate remote sales teams. His career spans more than two decades in sales, including corporate leadership roles, multiple ventures, failure, and scale. One of those ventures grew from the edge of bankruptcy into a business that generated tens of millions in revenue.
What’s notable about Kayvon isn’t just the growth. It’s how he approaches involvement. Even with teams in place, he continues to take sales calls and stay directly connected to revenue. Not because he lacks trust in his people, but because he’s clear-eyed about what control actually looks like in a growing company.
He’s seen what happens when founders outsource income too early. The business may look cleaner, but decision-making slows. Context erodes. The founder’s role shifts from operator to observer — often before the system is strong enough to carry that weight.
Where Founders Misjudge Leverage
Kayvon’s comments land because they point at things experienced operators recognize but don’t always say out loud.
“If you don’t use it, you lose it.”
Actionable insight:
Skills tied to revenue decay quickly. Even if you’re no longer the primary seller, staying active keeps judgment sharp and options open.
“I still take sales calls because I want to control my income.”
Actionable insight:
Revenue isn’t just cash flow. It’s information. When founders give that up entirely, they lose early signals about what’s changing.
“People stop doing the thing that got them busy.”
Actionable insight:
Success creates amnesia. As teams grow, founders have to deliberately preserve the behaviors that created momentum in the first place.
“Most people hire to get out of discomfort.”
Actionable insight:
Hiring to escape hard conversations or accountability weakens leverage. Hiring to extend capability strengthens it.
“Founder-led businesses make different decisions — because it’s their money.”
Actionable insight:
Ownership sharpens thinking. As organizations grow, founders need mechanisms that keep consequences visible, not abstract.
“Marketing didn’t save me. Sales did.”
Actionable insight:
Systems don’t replace contact. Especially early on, conversations still outperform dashboards.
What Not to Hand Off
There’s a version of scale that looks clean but feels hollow. Fewer meetings. More headcount. Less friction — and less feel. The founders who avoid that trap aren’t heroic or controlling. They’re selective. They know which parts of the business must remain close to the center and which can safely move outward.
Kayvon’s experience is a reminder that leverage isn’t about doing less. It’s about staying connected to the decisions that shape outcomes. The work changes as you grow, but responsibility doesn’t disappear. It concentrates.
If you’re hiring, scaling, or reorganizing, the useful question isn’t who can own this. It’s what do I need to keep understanding firsthand. The answer tends to matter more than the org chart.
Thanks for reading,
—Ryan
If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide
Ready for more?
Catch Kayvon Kay’s interview in its entirety on Eggs! The Podcast.
Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.
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Reading list
If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:
High Output Management — Andrew S. Grove
Still one of the clearest treatments of leverage, decision-making, and where managers actually add value.The Hard Thing About Hard Things — Ben Horowitz
A reminder that staying close to the hard parts of a business isn’t a failure of scale — it’s often the price of it.The Founder’s Dilemmas — Noam Wasserman
A sober look at how early choices around control, hiring, and ownership ripple forward for years.
More to explore
Kayvon Kay — https://kayvon.com
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