The Insight That Creates Freedom

I met Eric Partaker yesterday. Former Skype exec, runs a 200k+ subscriber newsletter. I was surprised when the topic turned to him asking about using Skyp for his webinar follow-ups. He runs about 20 webinars a quarter, gets hundreds of registrations per webinar, and wants to do one-to-one follow-up at scale. Classic use case for what we built–with maybe more people than most people get on webinars.

During this discussion, he asked a simple question of me more broadly: "What are you optimizing for?"

I started listing things. Skyp's growth. The advisory practice. The newsletter. Strategic partnerships. Each answer was technically correct. Each was also a dodge.

The conversation forced me to confront something I'd been avoiding. I wasn't building a focused company. I was maintaining a portfolio of related but distinct projects, each claiming to support the others. The advisory work informs the product. The personal brand drives awareness. The various content channels reach different audiences.

I was optimizing for optionality, not outcomes. Which meant I was not optimizing at all.

The Tyranny of Options

Founders love optionality. Keep the advisory work to pay the bills, and in case Skyp doesn't scale. Maintain the personal brand in case the company pivots. Write multiple newsletters to hedge our bets across audiences. Build relationships in three different directions in case one doesn't work out.

This isn't stupid. Markets change. Products fail (I will never forget). Hedging makes rational sense when you're navigating uncertainty.

One huge plus of raising venture capital is that it enables you–if not compels you–to put things down. With a salary, there’s no need for a side hustle. With a board, there’s no hiding from missed KPIs.

Optionality has a hidden cost that compounds daily. It’s the cognitive load you carry constantly—the mental overhead of maintaining multiple contexts, multiple identities, multiple stories about what you're building.

I had known I’d been paying this price for months. Every time I do a newsletter collab I write a byline–and it’s hard to keep it short. Because it isn’t. Founder/CEO of Skyp. Also advisor. Also newsletter author. What do I drive people to? Skyp? This newsletter? That newsletter?

Nothing was growing well because my own marketing wasn’t clear. I was treating Skyp like one priority among several. Writing content about general startup topics–that mentioned an email outreach product. Meeting potential advisory clients that might, actually, be good Skyp customers–but not bringing that up, because it was out of context. Building my LinkedIn presence as a general startup expert rather than specifically around GTM as the founder of an outbound tool. All reasonable activities. Just not focused.

The moment I admitted this to myself, something unexpected happened. I felt lighter.

Choosing what not to do isn't constraint. It's clarifying.

Focus as Freedom

Conventional wisdom says focus means constraint. You close doors. You narrow options. You limit yourself.

But I've realized the opposite is true. Focus creates freedom.

When you decide what you're actually building, you stop spending energy on maintaining facades. You stop splitting attention across multiple identities. You stop hedging bets that don't need hedging.

All that energy goes somewhere useful instead.

This is even true within a startup. When you put down that idea and allow yourself to just work on the core product, one or two features instead of all of them, you just feel better. Lighter, more focused, less crushed by the work.

So here's what I'm doing: I'm going all in on Skyp.

The advisory work continues with existing clients. It informs the product and I genuinely enjoy the work. But it's not the main thing anymore, and I’m not looking to grow it. Watch, I’ll get 3 referrals from this email.

The LinkedIn presence becomes a focused Skyp channel. Everything I write will drive awareness of the problem we solve, demonstrate expertise in the space we operate, or share lessons from building the company. If it doesn't serve one of those purposes, I shouldn't be writing it.

And I’ll give myself the freedom to invest the time so everything I write will be be a banger. By not having to do other stuff. Marketing is the work, sometimes, and this is the marketing.

The newsletters consolidate. Instead of maintaining separate identities—the thoughtful GTM advisor writing Seed to Sequoia, the company founder writing Skyp content—I am integrating them. This will help me clarify the messaging for those collab by-lines: Find Alex at Skyp. Period.

What This Means for You

If you're reading this, you're on the Seed to Sequoia newsletter. I've been writing it for founders, operators and VCs navigating early-stage growth for almost two years now. It's been personal, occasionally random, always authentic. I'm keeping it.

But I'm also moving everyone to the Skyp newsletter.

The Skyp newsletter is more tactical. It focuses specifically on outbound, sales enablement, and GTM execution—the things our product actually helps with. If you're building a sales motion, testing outbound channels, or trying to figure out how to generate pipeline without hiring an SDR team, you'll find it useful.

You might also find you don't care about those topics. That's fine. Unsubscribe. I mean that genuinely. Attention is the most valuable thing you have. Don't waste it on content that doesn't serve you.

The Skyp newsletter is designed to give people what they really want–not what I want to write, though obviously that has some influence. Really useful stuff. Which is why it gets a higher open rate than this newsletter–which already gets a very high open rate–and I get as many responses to each edition as I do here, with far fewer readers. In other words, it hits. I think you’ll like it.

Seed to Sequoia will continue, but less frequently. When I have something to say that doesn't fit the Skyp frame—observations about business, partnerships, the occasionally spicy take on market dynamics—I'll write it here. Think of this as the authentically random newsletter for insiders. The Skyp newsletter is the focused one, for everyone.

The Ask

Skyp is at around $10k MRR. Our goal is to more than double that by year-end.

When we hit $10k at the end of August, I was shocked. We set a goal to hit $25k by Christmas, which felt very doable. We had momentum. The product was working. Customers were seeing results. Doubling felt like a matter of execution, not luck.

Now it's mid-November. The goal is still within reach, but it's no longer comfortable. We need roughly $12-15k in new MRR to hit the target, which means closing 5-12 new customers in the next six weeks. Possible, but not guaranteed, especially with holidays coming up. The difference between hitting it and missing it is probably five conversations that go well.

Which means I need your help.

If you know someone building an outbound motion—founders doing their own sales, ops leaders trying to scale without hiring, revenue teams that need their reps to be more productive—share Skyp with them. Send them to skyp.ai. Make an intro. Forward this email. Whatever fits your style.

If you run outbound yourself and haven't tried the product, book a demo at skyp.ai/demo. We'll get you set up in 15 minutes. First campaign can be live same day. I did 4 demos last week; 2 people signed up and one is going through procurement. I like that conversion rate, just need to do more demos!

The product works. People who use it see results. We're not struggling because of the product. We're struggling because not enough people who have the problem know we exist.

That's solvable. But it requires more than me showing up on LinkedIn. It requires people telling others about it.

So if you've gotten value from this newsletter over the years—or even just this one post—here's how you can return it: tell one person about Skyp who has the problem we solve.

One person. That's the ask.

Focus Yourself

This time of year invites reflection. The year is ending. New planning cycles are starting. Companies do retrospectives. Investors review portfolios. Founders assess what's working.

You don't need a formal planning process to ask useful questions. In fact, formal planning processes sometimes obscure the real answers. They create structure that feels productive while avoiding the uncomfortable truths you actually need to confront. They put company before self.

So ask yourself: What's serving you? What isn't?

Not "what's interesting" or "what might be valuable someday." What is actively serving your most important goal right now?

What are you maintaining out of obligation rather than intention? What projects are you keeping alive because you spent time on them, not because they're the best use of your time going forward? What relationships are you preserving that don't generate anything meaningful? What content are you creating that nobody reads?

The sunk cost fallacy applies to more than investments. It applies to activities, identities, and commitments. Just because you've been doing something for a long time doesn't mean you should keep doing it.

What would you stop doing if you were honest about what actually matters?

This is harder than it sounds. We construct elaborate justifications for why everything we do is essential. We tell stories about how unrelated activities all support each other. We convince ourselves that maintaining optionality is strategic.

I am doing it right now.

Sometimes it’s true. Usually it's not.

Give yourself permission to stop things. To narrow. To commit. Not because focus is virtuous in some abstract sense, but because it's effective in a very practical one.

Every successful company I've studied had a moment where the founders went all in. They stopped hedging. They stopped maintaining backup plans. They committed completely to one direction and accepted that if it didn't work, they'd deal with that when it happened.

That's uncomfortable. But discomfort isn't a signal you're doing something wrong. Often it's a signal you're doing something that matters.

The insight that creates freedom isn't that you should do more. It's that you can do less.

And that less might be exactly what you need to break through.

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