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From Homeless to $20 Billion Deals: An Accountant’s Journey Through Automation

Blake Oliver · August 4, 2025 ·

Fifteen years ago, Devon Coombs was sleeping in his car. Skip ahead, and he’s helping negotiate $20 billion AI deals at Google Cloud. His story isn’t just another rags-to-riches tale—it’s a preview of accounting’s future.

I interviewed Devon on the Earmark Podcast, and what struck me wasn’t his remarkable turnaround. It was his pattern recognition. Devon lived through technology’s destruction of the music industry. Now he’s watching the same forces reshape accounting. The difference? This time, he’s riding the wave instead of getting crushed.

The Recording Studio That Technology Killed

At 18, Devon owned Antipop Records in North Hollywood. He’d grown up in foster care. His mother died when he was 15, and he never met his father. But he had talent and a passion for music, so he did what passionate people do: invested everything in professional recording equipment.

Then Logic Pro happened.

“My rates went from $50-100 an hour to competing with guys charging ten bucks,” Devon told me. “Musicians could record in their kitchen and get 90% of my quality.”

The 2007 recession started the bleeding. Technology finished it. Devon’s $100,000 studio became worthless overnight. He ended up homeless, sleeping in his car, trying to figure out what went wrong.

Here’s what he learned: Technology doesn’t destroy industries. It destroys intermediaries. Musicians who could compose, produce, and distribute music thrived with infinite digital instruments at their fingertips. Recording engineers and session musicians who only executed other people’s visions? They became extinct.

The Community College Revelation

While living in his car, Devon started taking business classes at Pierce College, a community college in the San Fernando Valley. He planned to become a music attorney. But accounting grabbed him instead.

“I was surprised by how much I liked doing the work,” he says. The profession also offered something Devon had never experienced: predictable career progression and financial security.

His first internship taught him an unexpected lesson. The CPA who hired him was successful despite being disorganized and barely keeping clients happy. “If this guy could make bank being this scattered,” Devon thought, “imagine what I could do if I actually tried.”

1,000 Cold Calls and One Big Bet

At Deloitte, first-year associates reconcile bank statements. Devon had other plans. He made 1,000 cold calls and emails to controllers across Los Angeles.

His pitch was brilliant in its honesty: “I’m new at Deloitte. I want to learn. Give me your time, and I promise you’ll get more attention from me than from any partner here.”

It worked. He landed GoGuardian as a client—one of the first ASC 606 implementations in the country. The partner told him it would never work. Nobody wins clients as a first-year associate.

Deloitte gave Devon a $100 bonus for bringing in a $100,000 client. That’s when he knew the Big Four model wasn’t for him. When Effectus Group offered to double his salary plus commission, he jumped.

Becoming the 606 Expert

ASC 606 was rolling out, and nobody understood it. The guidance ran thousands of pages. Most accountants waited for CPE courses to explain it.

Devon printed every page.

“I’d read 30 pages every night, then figure out how to apply it,” he explained. In two years, he completed over ten implementations across industries—software companies, call centers, and even nonprofits.

Six months into his new job, he won Automation Anywhere as a client. A multibillion-dollar unicorn choosing a boutique firm over the Big Four. Why? Because Devon knew 606 better than anyone.

“Put in six months of deep work on any technical topic,” he told me, “and you’ll blow everyone else out of the water.”

The AI Orchestrator Revolution

Today, at Google Cloud, Devon helps negotiate billion-dollar AI deals. But here’s what matters: He’s not just selling AI. He’s living the future of professional services.

“Agentic workflows,” he calls them. AI bots handle routine tasks while humans orchestrate the work. “You’ll have bots calling companies, and no one will know they’re bots. All those little tasks in between? Just bots talking to each other.”

It’s the music industry all over again. Technology eliminates executors and elevates orchestrators. The accountants who only know how to follow procedures? They’re the session musicians of the 2010s. The ones who can design systems, manage AI workflows, and apply judgment? They’re the producers.

Devon is now leaving Google for PCG (Principal Consulting Group), where he’ll build a practice around this orchestrator model. His goal: “better quality work with higher judgment applied with all my expertise and one-tenth the cost.”

Your Window Is Closing

Recording studios were given years of warning, but they ignored it. By the time musicians started canceling sessions, the game was over.

Accounting firms today are experiencing the same warning signs: clients questioning fees, staff leaving for tech companies, and AI tools handling basic bookkeeping. The script is playing out again.

But unlike Devon’s recording studio, we can see it coming. We can choose to be orchestrators instead of executors. We can build practices around AI enhancement instead of human grinding.

The transformation isn’t some distant future. Devon’s already building it. He’s creating an entirely new service model where CPAs orchestrate AI agents to deliver superior results at a fraction of traditional costs.

“The AI movement is our chance to add real value,” Devon insists. “But only if we lean in now.”

Listen to the full episode to understand how to position yourself for this shift. Because Devon’s journey proves one thing: Those who embrace disruption don’t just survive. They discover possibilities they never imagined existed.

The question isn’t whether AI will transform accounting. It’s whether you’ll be the orchestrator or become obsolete. Devon made his choice. What’s yours?

Podcasts Accounting Tech, AI, Blake Oliver, Devon Coombs, The Earmark Podcast

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