Phil Dakin: from outcome-driven to Internally grounded

Founder: Phil Dakin, Co-Founder
Stage: Pre-seed → early revenue
Engagement: Combined individual and group coaching through lume’s Performance and Team Labs

The noise of the early stage

When Phil Dakin joined lume’s Performance Lab in early 2024, his company, Wayside, was still finding its footing. Wayside builds an AI Assistant for PEOs, automating repetitive workflows and integrating across tools like Outlook, PrismHR, and iSolved. The team had just raised a $1M pre-seed and was sitting at around $50K in ARR.

From the outside, things looked promising. On the inside, it felt heavier.

“We were making a lot of proposals but not closing deals. We’d found early traction in one direction, but the market wasn’t validating it. It felt like we were constantly working hard on things that weren’t working.”

Phil and his co-founder were stuck in the awkward in-between, post-raise but pre-clarity. It wasn’t burnout. It was the slow drain that happens when the effort-to-progress ratio gets out of balance.

“You’re showing up every day, but most of what you’re working on isn’t working. That’s hard to sustain.”

When identity and output blur

Before lume, Phil’s performance patterns were shaped by environments where high effort always produced high output. He equated momentum with self-worth.

“I’d always performed well, school, career, leadership roles. So being in a place where the business just wasn’t working made me question myself more than I expected. You go from structure to chaos, and suddenly every missed deal feels personal.”

That mindset became a quiet tax. It blurred his thinking, weighed down decisions, and made every business fluctuation feel like a personal one.

“You wake up asking yourself, ‘Should I even be doing this?’ It’s hard to execute when that’s the question in the background.”

A structured reset

Phil came to lume looking for something different from therapy or advice. He wanted a system to help him rebuild how he worked, made decisions, and understand his own patterns.

His program included two parts:

• Founder performance coaching focused on clarity, mindset, and execution

• Health coaching focused on relationships, balance, and emotional grounding

“I’d done therapy before, but what I wanted was someone who could help me think about both life and business. Coaching felt like the right balance of reflection and precision.”

Inside the lab: rewriting the operating system

Inside lume’s lab, Phil started rebuilding the internal systems that shaped his leadership.

1. Building curiosity as a performance habit

Instead of shutting down doubt, Phil learned to follow it.

“Before, if I had a thought like, ‘Maybe this isn’t working,’ I’d shut it down. Now I pull the thread, talk to people, test the idea, understand what’s behind it.”

That curiosity became part of his operating rhythm. It changed how he evaluated customers, how he approached product decisions, and even shifted how his team collaborated.

2. Upgrading communication and alignment

Coaching also reshaped how Phil communicated with his co-founder. He practiced being clearer, more grounded, and more direct, especially during moments of tension or change.

“I’ve spent full sessions workshopping how to communicate something difficult or strategic. Those conversations directly changed how we operated, and they showed up in outcomes.”

That clarity spread across the company, improving product cycles, hiring, and execution.

Building stability outside the business

Alongside founder performance coaching, Phil met with a lume health coach to work through relationships, friendships, and the personal transitions that come with your late twenties.

“I turned 28 this year. A lot of people around me are getting married, having kids, moving home. Talking through that helped me understand what matters to me personally, not just professionally.”

The personal work grounded him. It strengthened his emotional bandwidth and made him more present as a leader.

“When you’re not questioning everything about your life, it’s easier to lead your company.”

It also gave him something founders rarely have early on: stability outside the business.

Internal stability → external growth

The internal work showed up in the metrics. Within a year, Wayside 15x’d its revenue, made its first in-person hire, and shipped a more confident product.

But the real transformation was internal.

Phil stopped moving between doubt and overdrive. He started leading from a centered baseline that didn’t collapse under pressure or uncertainty.

“It’s easier to show up when you stop questioning the game you’re in.”

His decision-making became sharper, his communication cleaner, and his recovery faster. What changed wasn’t just how he worked, it was how he thought about work.