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Lily Chang

Lily Chang

Lily Chang is Secretary-Treasurer of the Canadian Labour Congress (CLC), the first worker of East Asian descent elected to CLC office, and a longtime CUPE Local 79 leader.

Sep 30, 2026

2:29
They just didn't buy it? It
2:31
wasn't disbelief.
2:33
It was prudence.
2:34
A blunt debrief later made it obvious.
2:37
They weren't shopping for a lottery ticket.
2:39
They wanted a partner.
2:40
They needed a careful, likely path to profitability in the first 18 to, wait, 24? No, 18 to 24 months.
6:33
What's in that briefing?
6:10
That obsession beats a slick UI or a cute algorithm as a predictor of success.
6:16
Totally.
6:17
It's a stand-in for resilience.
6:19
But I have to ask.
6:21
Some of my companies tackled smaller stuff, not fire-breathing monsters, more like sand in the gears.
6:27
If the issue is just inefficiency, does this framework risk sounding overwrought?
7:19
That only lands after you've made the problem stark enough that any other path seems irrational.
7:26
My biggest takeaway isn't even about investors.
6:01
What does that look like when it happens?
6:05
Instead of you shouting, market size $50 billion, they're thinking, my cousin's a freelancer like Sarah.
6:13
She vents about this constantly.
6:15
How many people like her exist? You made Tam personal, not a line from a Gartner report.
6:55
you see the fit?
6:57
The story is the lens on the spreadsheet.
7:01
If I believe in Sarah Saturdays, I'm not just staring at CAC.
7:06
I'm looking at the cost of giving weekends back.
6:06
Do you see a case for that?
6:08
Well, I think that's very speculative, right? So I don't know that that's going to be true.
6:12
What I do know is that privatizing always leads to higher costs, poor service, bad effects for workers, you know, and, you know, we know that we have several examples of that already happening.
6:26
And, you know, this is not something new that we've heard before.
6:31
I mean, we've got these examples of airports and in our report, really like every single example pretty much is a failure.
6:39
These private investment companies are really, really good at what they do.
6:42
They're not going to put their money, billions of dollars into something unless they can actually see a very clear line for a good profit in a short term, right? So cost will go up in the flights, but also in all kinds of other things that happen at the airport, whether we're talking about the retail outlets or the food restaurants that are there, their costs will go up, so it'll be passed on to the consumer.
8:21
Do you see the government walking this back at any point, given where they're at and what they've said?
1:24
That kind of signal money can't buy.
1:27
Question though, is it always a community or sometimes just a swipe and move on? There's that classic wisdom of crowds effect.
1:37
People treat crowdfunded goods as pre-vetted, which helps and also adds pressure.
3:52
Fiduciary duty spikes overnight.
3:55
And the rulebook shows up.
3:57
For a long time, public solicitation was off-limits for good reasons.
4:02
Fraud.
4:03
Hype.
0:34
It keeps reminding me the pivotal variable isn't always living in the spreadsheet.
0:39
And I'm Lily Chang.
0:42
For me, it wasn't a curiosity.
0:45
It was a bruise.
0:46
Early on, I worshipped my model and ignored the human across the table.
0:51
Turns out you don't pitch a balance sheet.
0:54
You're dealing with a person, which means psychology walks into the room first.
5:35
Now, the endowment effect tilts toward you.
6:29
Walk me through it.
6:31
You don't just hunt talent locally.
6:33
You sell the place to the talent.
6:35
If you're recruiting a PhD from Boston and not one founder begging them to move, you're an ambassador for a different life.
6:44
You line up time with the mayor, get the school board head to talk through options for their kids, have that restaurateur host a dinner, make it a community courtship.
7:49
Does the chamber president on your side actually move valuation or terms?
7:54
Yes, but not because anyone's sentimental.
7:58
Investors optimize for risk.
0:35
The idea that tech might finally fix that, I've been waiting on it a long time.
0:41
Lily Chang, hi.
0:44
For me it's not abstract.
0:46
I've lived the hundreds of emails into the void thing, hoping one person actually reads past the first line.
0:53
If we can swap guesswork for a data-first approach, that shifts who has leverage.
0:58
It feels different.

7 MINS LATER

8:01
You finally see the path.
8:04
Exactly.
2:12
What happened?
2:13
The first 45 minutes weren't about the spreadsheet at all.
2:17
They asked about his background, family, why he started, how he leads, everything except the metrics.
2:23
He got antsy, kept yanking the conversation back to slides.
2:27
They read it as impatience and honestly, a bit transactional.
2:31
He walked out thinking, total waste, not serious.
2:35
Their note back, we didn't feel he was someone to build with.
3:13
power distance how does that change the pitch in the room
1:45
And once you control for IQ and the big five, say extroversion or conscientiousness, the predictive power for leadership can look like smoke.
1:56
I get that critique.
1:58
A lot of early tools were flimsy, self-reports that invite people to check the right boxes.
2:04
But here's where academia and the room diverge.
2:06
Maybe EI overlaps other traits, but deploying them under heat, reading a room in real time and adjusting your approach, that's a learnable skill.

6 MINS LATER

8:26
Thank you.
8:27
Loved it, David.
8:29
And one last thing to leave hanging in the room.
0:24
I keep meeting founders with sharp ideas who stall, not because the concept is weak, but because the guidance around the gnarly moments is missing or mis-aimed.
0:36
I'm Lily Chang.
0:38
Same.
0:39
In my first company we brought in a marquee advisor and thought we'd struck gold.
0:44
His input didn't match our reality, we bled time, and momentum vanished.
0:49
That bruise is why I care so much about this.
4:33
What did you learn from the ones who bailed? My
4:37
best advisors did homework before we even spoke.
0:32
And yeah, this one keeps me up.
0:35
I'm Lily Chang.
0:36
It kept me up for years.
0:38
When I was building my first company, every door looked like a VC door.
0:43
If you didn't fit hypergrowth, you were just out.
0:47
Brutal.

5 MINS LATER

6:05
You can match capital to the company you want to build, not the one a fund needs you to build.
6:11
And it builds better habits.
3:38
So what did you change, practically, in the room?
3:42
First, we panicked for a week.
3:44
I'll tell the truth.
3:46
It was like building a race car and then being asked for city MPG.
3:51
Then we stripped the model down and rebuilt it around one target: reach cash flow positive with this round, not some hazy exit ten years out.

7 MINS LATER

10:56
Let's post the resources on the site and circle back in two weeks to tackle the next hairy problem.
11:02
Deal.
11:03
Adapt, stay pragmatic, and back your own resilience.
4:26
Are those interchangeable?
4:28
Not quite.
4:29
Formula funding usually flows to states or localities based on a law.
4:33
Population, income levels, that kind of thing.
4:36
Founders don't apply for those directly.
4:39
Project funding is the sweet spot.
4:41
You propose a scoped project with a timeline, and it's awarded competitively on merit.
6:17
Is that a realistic path for a startup?
5:53
Why not?
5:53
Because all the examples that I have, just in my own backyard in Ontario, for example, uh, tell me that privatization actually leads to less accountability, less accessibility, and-Worse in terms of safety.
6:07
So, um, you know, there's lots of examples we can talk about later, but certainly I don't believe that privatizing the airports fully, um, will do that.
6:16
I think that it'll bring in higher costs, because we will have private corporations that are accountable to their shareholders, to their investors, and they will demand a return on their money.
6:27
Um, I also think that there'll be less, uh, public oversight, there'll be less accountability.
6:32
Um, it'll be decisions made behind closed doors, um, in a, in a, in a closed corporate boardroom as opposed to in a, in a board, for example, which happens right now and, and, uh, comprised of, of people who are in the community, who have a stake, um, in, in that particular service.
6:47
So I don't think, um, that that would work at all.

6 MINS LATER

12:43
Um, if the federal government follows through on this, Lily, what could it mean for airport jobs?

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