What's up, it's Zayd

Someone DM'd me a few weeks ago after seeing Valley's January numbers.

"Must be nice to have it all figured out."

If real life was an episode of The Office, I would have done a wildly dramatic spit take...in retrospect, I kind of wish I did, but our lead engineer would have probably quit if I got cold brew all over his keyboard.

Regardless, "figured out" is maybe the last phrase I'd use to describe building Valley. Survived, stumbled through, white-knuckled. Literally any of those would be more accurate.

There's this myth in “Founder World” that the path from zero to traction is a clean line going up and to the right. That if you just follow the right playbook and have the right idea, things click into place relatively fast.

In reality, the path looks more like a heart monitor during a panic attack. It’s jagged and unpredictable and occasionally flatlined.

This week, I want to share the actual timeline. The anti-highlight reel.

Forwarded this email? Get Enabled in your inbox each week.

My favorite finds of the week

My first "business" was buying apples and oranges from the kitchen and selling them door-to-door at a 200% markup. I am so serious. That was the entire business model. If you'd told 14-year-old me that this would eventually lead to raising $3.2M from investors like General Catalyst and Jason Calacanis, I would have asked you what General Catalyst was.

I co-founded Advisor Appointments, an appointment-setting agency helping financial advisors connect with executives. We grew it, employed over 100 people worldwide, and eventually sold it. That's the "sold my first startup" line people see on LinkedIn and assume was a straightforward journey.

That couldn’t be further from the truth. There were months where payroll was a coin flip. Clients who ghosted after promising big contracts. Team members I trusted who made decisions that cost us accounts. The exit happened, but the path to it was chaotic.

When I joined Antler's accelerator, I was building Fish (a social network for VCs and founders). I loved the idea. My lead investor told me he hated it.

He was right. I just didn't want to hear it yet.

Fish went to investment committee. One person liked the business. Six others said "I don't like this business, but wow, that's a great founder." Most VCs would have passed, but Antler backed me anyway (despite the idea).

Fish grew a little. It attracted investor meetings, but there was no world-domination energy and I knew in my gut it wasn't going to be The Thing.

Then I ended up in the hospital with kidney stones. Instead of resting like a normal person, I started building what would become Valley.

I called my investor from the hospital bed: "I think I'm going to pivot. AI SDR." His response: "Ok, you know what I'm going to say. Tell me why I'm wrong."

We debated for hours. First principles. Why me (appointment-setting was my entire background). Why now (AI had just unlocked what I used to do manually). Why this could be massive (the market has multiple billion-dollar winners like Apollo, ZoomInfo, Gong, Outreach, Salesloft).

The pivot happened. Within 30 days we had an MVP, first paying customers, and a team that was fully aligned.

Fundraising was brutal. 136 investor meetings before someone said yes. Most founders give up around 50. There were weeks where every single call ended with some version of "we love you but the space is too crowded" or "AI wrappers aren't defensible."

But there are 8 billion people in the world. A few of them had to say yes.

Eventually we raised $2M+. Then later, a follow-on where I emailed existing investors on a Wednesday and had $1.2M committed by Friday.

The difference was proof. We had customers, revenue, and traction.

We lost 30% of our users in a single month. The product just wasn't reliable. I was heads-down implementing operational frameworks (EOS, OKRs, all of it) while customers were churning because the core product didn't work.

That was rock bottom.

I wrote about this in the Anti-Playbook newsletter, but the thing I didn't fully convey is how it felt. You question everything. Your judgment. Your team. Yourself. Whether the whole thing is going to implode.

We went back to basics. Fixed the product. Focused on revenue. Cut the team. Threw out every framework that wasn't directly tied to moving the needle.

The results were 5x YoY revenue growth, $128M+ in pipeline generated for customers, record months, and 350+ demos in January alone.

That only happened after a decade of building things, breaking things, selling things, pivoting, getting rejected 136 times, and losing 30% of our users in a month.

That's the real, messy, honest timeline.

Examples of the best performing LinkedIn outreach messages

This is the question I get asked most, and it's the one I find hardest to answer because the line between persistence and delusion is so thin, and some days I don’t know which side of it I’m on. That said, here’s the framework I use to check now:

Are you getting closer to signal or further from it?

With Fish, every conversation moved us further from clarity. We'd talk to potential users and hear polite enthusiasm but no urgency.

With Valley, the very first conversations generated "when can I test it?" and pricing discussions.

Persistence is worth it when each iteration brings you closer to product-market fit signals. If each iteration just generates more questions, that's a different kind of data.

Is the problem getting more painful or less painful in the market?

The problem Fish solved (connecting founders and VCs) was getting easier to solve through existing platforms. The problem Valley solves (scaling quality outbound without massive headcount) was getting more painful every quarter as email limits tightened and buyer expectations rose. Ride tailwinds, not headwinds.

Can you be honest about your energy?

When I was forcing Fish, my energy was performative. I was hyping it to investors and to myself. When I started building Valley from a hospital bed, nobody asked me to do that. The energy was intrinsic. Pay attention to where your energy is coming from and if you have to convince yourself to be excited, something's off.

Are customers pulling or are you pushing?

With Valley, organic word of mouth started almost immediately. People who received Valley-generated messages were so impressed they asked how to get it for their own company. That's pull. If every single customer requires convincing, persuading, and discounting, you're pushing a boulder uphill.

The part that gets lost in the "overnight success" narrative is that the emotional toll is real, and it's cumulative.

After 136 rejected fundraising meetings and losing 30% of your users, you don't just "learn from it" and move on. It’s not that easy to shake that off. These things accumulate. They change how you make decisions, how you trust people, how you sleep. At some point, every founder I know has pretended they're fine, and the pretending makes it worse.

The founders who last are the ones who are honest about the difficulty, find people who understand it, and keep showing up anyway.

If you're in the middle of the rejection phase, the nothing-is-working phase, the am-I-delusional phase right now, I'll just tell you that I've been in all three, sometimes in the same week, and the company is still here.

The messy middle is the whole game.