😎 He got fired twice, so he signed 20 clients. Billionaire's advice for 21 year old. Trades > tech?

SELLER’S SECRETS

He got fired twice, so he signed 20 clients — Kellen Casebeer

Kellen Casebeer is the founder of The Deal Lab, a boutique GTM agency for B2B companies who can’t stand sloppy mass cold email campaigns. Over the last couple of years, he’s grown a dedicated team of seven and his client base to 20+ at times.

The genius behind some of the best B2B prospecting in 2025 is on full display in our full 1-1 podcast interview here.

Product-market fit? Nah.

Message-market fit.

Fired for doing his job… well?

Kellen’s start in sales really began well before this fancy tech-y stuff he’s up to now.

If you needed low voltage electrical work done in the Bay Area, he was your guy. Starting as a tech, climbing the ranks, to later running his own business for three years, he ultimately shut this down to go get “real” sales experience that’d better prep him for his hopeful tech sales career post-college.

So he went to sell gym memberships. Then office furniture rentals.

Now that may not seem all that relevant to tech sales, but what was relevant was the sheer amount of time he’d spent selling to this point.

Seven years.

(Oh yeah, did we mention he dropped out of high school at 15?)

He goes back to finish school at San Francisco State before he lands his first tech SDR role. He finally made it, right? The childhood dream was achieved.

Nope.

Manager quit the week prior. Was handed some cookie-cutter outreach scripts. A severely underwhelming moment at the time.

Now despite the rocky start, Kellen still pushed his way into a full-cycle AE role, then rolled that experience (through a couple others) into a VP of sales role for a small GTM agency

One that just so happened to have a hardcore Traction EOS guy as COO. Link here if you’re not familiar with the operator’s bible.

This rigid EOS-driven COO was forcing processes Kellen knew wouldn’t work when it came to B2B sales/marketing.

One thing led to another, and he was let go.

The same wedge that got Kellen fired, was the one that propelled him into starting his own business just two months before his first son was born.

Between that and his California mortgage, the pressure was on to say the least.

Two babies. One year.

Pressure makes diamonds right?

I mean, starting a company and having your first son within a couple months of each other is no easy feat.

When worse comes to worse, Kellen did what Kellen does best.

Outbound.

If you have a B2B business and knew Kellen when he first started Deal Lab, you probably heard from him

It was truly a “by any means necessary” scenario when signing his first clients that kept everything afloat.

"I will kill myself to make this stuff work. I will just do every single thing and it’s clear in how I sell it, it’s clear in the delivery as people are experiencing it... I’m an idiot who will just keep going."

Mortgage paid, credit cards paid, son healthy, business growing.

In hindsight, it’s no surprise.

Winners win.

Some past cold email sorcery on display for you

His client’s product: Drones to campus security for first responder use cases.

Here’s the process he uses to run relevant B2B outreach, all triggered by pre-set keywords that show a campus safety incident via Google Alerts.

• A campus safety incident occurs and is flagged through Google Alerts.

• Clay is used to enrich leads from said affected campus with relevant context. It also pulls in useful context, like how long they’d been in the role or what kind of campus they manage.

• Identifies decision-makers via Apollo.

• Tailored messaging is crafted to reference the unique incident, team members, and tie it to drone use cases.

• Cold outreach is launched using Instantly for sending.

• A LinkedIn touchpoint is added to warm up contacts further.

• He follows up and tracks responses, using insights to refine messaging quickly.

• Conversations convert into demos by showing drones as cost-effective safety upgrades.

And to think Kellen was selling $100,000 websites for his clients before all of this cool AI stuff was even around.

The possibilities with AI are truly endless right now. This article is an honest attempt to showcase some of Kellen’s game, but man.

You guys just need to watch his podcast interview for the full rundown.

Action Items: Do what Kellen Does

How Kellen finds “message-market fit” for outbound prospecting

• Track recent events your prospects care about (e.g. news, funding, hiring).

• Rewrite messaging to match their current pain—not your generic pitch.

• Use “You probably saw…” or “After [event], teams like yours…” to hook.

• Test fast. If nobody replies, you missed the moment or the message.

How Kellen is using AI for elite data and personalization

• Clay + ChatGPT to generate custom lead context + enrichment.

• Auto-draft flexible first lines or emails using enriched inputs.

• Feed call transcripts into AI to extract objections for follow-up contact.

• Let AI prep, then human-edit for relevant tone and clarity.