Penny Dizad and the Business of Live Nights
By Stephen Cyrus Sepher
How Pegasus Concerts builds touring shows that feel effortless to the audience
There is a moment at every good live show when the room forgets the week it just survived.
People walk in carrying deadlines, family pressure, bad news, and noise. Then the lights go down, the stage takes over, and for ninety minutes they get to be somewhere else. That is the product. Not tickets. Not posters. Not even the artist’s set list.
The product is relief. Precision. An experience that lands.
That is what Penny Dizad has been building through Pegasus Entertainment and Events, operating across Toronto and Los Angeles.
This conversation narrative is built from our podcast discussion, but I am writing it with one goal: laying the groundwork so other business owners can see what a serious operator actually does behind the scenes, and why that mindset translates far beyond entertainment.
She did not start in live events
Penny’s original dream was film. She came through film school in Canada, then moved to Los Angeles in 2014 with a simple plan: save money, show up, get work.
Early on, she landed on real sets, including a music video with Snoop Dogg and days on the Steve Jobs movie with Danny Boyle. It mattered because it taught her a truth most people do not learn until later:
Your resume grows faster when you stop waiting for permission and start building proximity.
She reached out to comedian Max Amini within her first year in LA, coordinated his show, then moved into booking and producing. Over time the scale changed. The job changed. The responsibility changed.
But the core stayed the same: build the night, protect the night, deliver the night.
Pegasus is a touring company, not a vibes company
On the Pegasus Concerts site, the positioning is clear: live events, concerts, standup comedy, and theater.
They also operate with real infrastructure: offices listed in Toronto and Los Angeles, plus a public contact line and business email.
That matters.
Most people think “event business” means planning. What it really means is operations.
It is permits. Routing. Crew. Ticketing systems. Marketing. Contracts. Venue negotiation. Tour accounting. Travel contingencies. Audience flow. Security. And the part nobody posts about: what you do when something breaks an hour before doors.
Pegasus has a public policy page warning customers to buy tickets only through the official ticket pages listed on their website. That single detail tells you they have dealt with the real world of resellers, scams, and brand protection.
The key decision is always the same
Penny explained her touring decisions in a way every business owner will recognize.
It is never only about taste, and never only about money.
It is a balance between what she believes in and what can actually work financially, because many of the shows are produced in-house and self-funded. That forces discipline.
A good operator does not confuse passion with a plan.
Culture changes the deal
One of the strongest parts of the episode was her breakdown of international differences.
In North America, negotiation often looks like: “Let’s meet in the middle.”
In parts of Europe, she described it as: “This is our number. Take it or leave it.”
In the Middle East, the complexity jumps. She talked about permits that can require relationships, in-person approvals, and unpredictable timelines. She also described the added layer for comedy: content restrictions and the need to demonstrate what the performance will be like before approval.
If you run any business that crosses borders, this is the entire lesson:
You are not negotiating with a person. You are negotiating with a culture.
The business is simple. The work is not.
Penny said she toured heavily before the pandemic, then rebuilt her system after.
She hired a team. She split responsibilities. She learned what can be handled remotely and what must be handled on the ground.
That is not an entertainment lesson. That is an operator lesson:
If your company only works when you personally show up, you do not have a business yet. You have a job with a brand name.
The audience experience is the real competitive edge
Penny made a point that stuck with me.
In film, you control the story on screen.
In live events, you do not control the artist’s performance in the same way. The artist has their vision. Your control is the experience from A to Z: how people enter, how they feel, how the room is managed, and how they leave.
That is exactly how real brands win too.
Most companies obsess over the product. The smartest ones obsess over the customer’s entire emotional path.
That is what creates repeat business.
Proof looks like dates, venues, and execution
Pegasus publicly lists upcoming and past events on their site.
And they show real-world event listings tied to their organizing work, like a May 9, 2026 show at the Fine Arts Theatre in Beverly Hills, with schedule blocks and organizer contact details.
This is the part business owners should notice:
A serious company leaves a trail of execution.
Not posts. Not promises. Executed nights, documented publicly.
Why this matters to other businesses
If you run a dental office, a law firm, a fitness studio, a med spa, a restaurant, a real estate team, or a private aviation company, the Pegasus model translates cleanly:
Build trust through repeatable systems, not charisma.
Protect your brand through clear policy and clean customer flow.
Separate taste from viability, and make decisions with both.
Design the full experience, not just the deliverable.
Create a team structure that can operate without your constant presence.
The live event world punishes sloppy operators fast. That is why it is such a clean case study for any service business that wants to scale.
Closing
Penny’s work sits at the intersection of production discipline and cultural fluency. It is not glamorous when you are building it. It becomes glamorous only when it works.
And when it works, the audience never sees the machine.
They just feel the night.
If you enjoyed this narrative, subscribe to the newsletter. This is part of The Conversation Podcast, a storytelling series exploring the human side of art, technology, and ambition.
