In this episode of the EO San Diego Podcast, host Jason Lee and co-host Marc Gallo sit down with Les Kollegian, CEO of Jacob Tyler, to talk about entrepreneurship, the power of branding, and how EO helped him navigate the highs and lows of building a creative agency from scratch.
From working out of friends’ New York apartments to building a nationally recognized brand, Les’s journey is anything but traditional — and it’s exactly that unpredictable path that helped shape who he is as a leader and creative thinker today.
From Vivid Commerce to Jacob Tyler — A Personal Rebrand
Les didn’t set out to become an agency owner. After leaving a traditional agency, he launched Vivid Commerce as a way to freelance and build a portfolio. But when his son was born in 2003, Les rebranded his company to Jacob Tyler — his son’s name — and infused it with personal meaning and intentionality.
“I thought, okay, Jacob Tyler will be to design what Kenneth Cole is to clothing — a great experience, you look good, and it’s reasonably priced.”
That mindset of delivering premium experiences with authenticity continues to shape the agency’s ethos today.
Why Branding Is Storytelling, Not Just Design
Les’s foundation in working with premium brands like Ritz-Carlton and Four Seasons taught him one of his most important lessons: great branding starts with values and story — not visuals.
“If your employees understand your company’s values, they’ll know how to make the right decisions on your behalf.”
Les applies this philosophy both internally and to every client relationship. To him, branding is a voice, a personality — and it has to match the experience you deliver.
Finding EO (And Kicking Imposter Syndrome in the Teeth)
Les joined EO San Diego in 2011 after a quirky turn of events involving a rental condo and a very full house of entrepreneurs. While he felt like an imposter at first, the relationships he built through his forum were a game-changer.
“I felt like the dumbest person in the room, and I kinda liked that.”
Through his EO forum, Les not only built lifelong friendships — he also found a support system that pulled him back from the edge when business got tough.
“There’ve been times I’ve just wanted to walk away. And my forum has literally dropped everything for emergency meetings and whiteboarded solutions with me.”
Lessons in Scale, Hiring, and Letting Go
Like many entrepreneurs, Les admits he struggled with scale and hiring. He trusted too easily, waited too long to let people go, and learned (sometimes the hard way) to “measure twice, cut once.”
“No one’s ever said, ‘I should have held on to that person longer.’”
Now, Les is focused on building the right team and moving closer to a scalable model that doesn’t require him in the room for every big decision.
Why EO Events Matter (And Why You Should Go Anyway)
Although Les admits not every EO event has been life-changing, he sees their value in deepening relationships and discovering new perspectives — especially outside of your forum.
“You can go to 20 events and still only get five minutes with someone. That’s why I always say, ‘Let’s go to lunch.’ One-on-one time is where the magic happens.”
He believes that to truly get the ROI from EO, members need to show up — for the events, the board, and for each other.
What’s the Real ROI of EO?
Les puts it simply: the return isn’t just financial — it’s personal, relational, and sometimes even lifesaving.
From selling a property quickly thanks to an EO connection, to finding a trustworthy contractor after a renovation disaster, EO has provided Les with solutions he didn’t even know he’d need.
“Relationships are everything. That’s the real ROI.”
Final Takeaway:
You don’t have to have it all figured out to belong. Whether you’re celebrating a win or navigating a rough patch, EO is a place where entrepreneurs like Les find clarity, community, and real-world solutions.
“Everyone’s got imposter syndrome. But in EO, you learn you’re not alone — and that’s everything.”
Listen to the full episode to hear more about Les’s journey, his thoughts on leadership, and why he’s a lifelong EO believer.