From W-2 to WTF Took So Long? Why I’m Joining Kyle & Co

For most of my career, I’ve been a good little corporate soldier. W-2’d up, PTO accrued, stock options offered (and rarely vested). I’m risk averse, believe it or not, even if my public persona would lead you to believe otherwise. 

And it’s been…well, same shit, different employer, for at least a decade or so. Kind of like the industry I’ve grown up in.

I’ve been the guy in the background these past couple of years: the one writing the press releases, crafting the analyst briefs, or quietly ghostwriting for the folks you see quoted in Forbes Online, or developing collateral that only advances a pipeline, and not a profession. 

I’ve done the work of an analyst for years: deciphering vendor roadmaps, calling out B.S. marketecture, telling founders their pitch decks were a mess, and politely explaining that “AI” does not, in fact, mean “automated intake.”

But I’ve always done it from inside the machine. And while I might be a contrarian, being an at will employee means I’ve always been very much a cog in said machine.

So why now? Why this leap? Why Kyle & Co?

Well, let me tell you a story.

A Collective Leap of Faith

Kyle Lagunas has been one of my closest friends (and fiercest sparring partners) for over a decade. Emily Wares and Brandice Payne are two of the sharpest minds in the industry, and two of the most competent colleagues I’ve ever had the privilege to work with. 

These are people who’ve challenged me, inspired me, and kept me honest. They’re not just colleagues. They’re the kind of people you’d start a band with… if that band was really into HR technology and private equity strategy.

When Kyle said he was starting something new, it didn’t feel like a job offer. It felt like a jailbreak.

Kyle & Co isn’t trying to be a traditional analyst firm with an identity crisis. There are no velvet ropes. No overpriced access passes. No paywalled “magic” graphs that look like someone spilled soup on a quadrant chart and called it insight.

Instead, we’re building a practice that actually reflects how this industry works. One that connects the dots between capital, product, and people. One that takes a practitioner’s lens, not a PowerPoint deck, and puts real context behind the noise.

We’re not here to tell you what you already know. We’re here to say what everyone’s thinking, backed by data, fieldwork, and decades of collective experience.

And gratuitous use of the royal “we.”

Traditional Analysts: Always Predicting Rain, Never Getting Wet

For too long, the analyst game has been run like a cable news panel: lots of airtime, not a lot of skin in the game. 

There are analysts out there who haven’t recruited a candidate, run a campaign, or built a product in years – but they’re still somehow telling everyone else how to do their jobs.

These are the same folks who told you skills were the future of work… in 2004. 

Who say “platform play” like it’s a product strategy and not a Squarespace template. Who named 43 different vendors in their latest “Top 10” list. Who passed the mandatory retirement age at Deloitte when I was just beginning my career, and whose material and mindset are just as expired (on a maturity model, they’d be in the assisted living phase).

The emperor has no clothes, folks – and frankly, they never even hired a stylist. Maybe a plastic surgeon.

Kyle & Co is different. We’re small, scrappy, and actually doing the work. We talk to founders every day. We sit in product demos, dissect investor decks, help PE firms evaluate buy-side targets, and yes, we still get on the phone with recruiters. 

Because that’s where the story is. 

That’s where the truth is.

Cashing In My Chips

This isn’t just a career move. It’s a mindset shift.

After years of telling founders to take risks, bet on themselves, and think differently… it was time I took my own advice. I’ve built brands, led turnarounds, survived acquisitions, and lived through enough RFPs to know that the real power doesn’t come from having a title. It comes from having a voice.

I’ll be focused on the messy, fascinating, ever-evolving intersection of recruiting, technology, and capital. Startups. M&A. PE and VC. Strategic partnerships. Everything that moves the market, but rarely gets covered beyond the press release.

It’s not just about who raised or who got acquired. It’s about why, what it means, and what’s next.

An Open Thank You

To the recruiting community: thank you for keeping it real, for building despite the headwinds, and for always calling B.S. when you see it.

To the vendors: keep pushing. Keep innovating. And if you’re ever not sure where you stand, give us a call. We’ll tell you.

To the analysts clinging to their charts and conferences: we’re not here to replace you. We’re here to make you better, by making the conversation a little more honest and a little less pay-to-play.

And to Kyle, Emily, Brandice and team: thank you for creating a place where I could finally stop playing it safe.

Let’s shake things up.

Follow along at kyleandco.com or hit me up directly. I’ll be the guy reading 10Ks like they’re tabloid gossip, whispering sweet nothings to your Series B pitch deck, and still trolling LinkedIn like it’s a competitive sport.

I can’t wait.

Kyle & Co · Insights

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