Episode #33 - Anson Wu

#15MinuteFounder

Anson Wu kept going to startup events and leaving with nothing.

Hustle culture was at its peak, and speakers made success sound like luck: they met the right guy at the right time and stumbled onto the right opportunity. Anson was working just as hard and moving slowly. When he talked to other people in the audience, most of them felt the same way.

So he started Ugly Talk, a national event series where founders talk about how they messed up, what they learned and why they pivoted. It began in Chicago and has since run in New York, Miami, Los Angeles and San Francisco, with London, Paris and Toronto next on the list.

In this episode of the 15 Minute Founder, Anson shares the most common “ugly moment” he hears from founders and the mistakes he made building Ugly Talk itself, down to a producer who forgot to hit record.

He also explains how a free, invite-only event series makes money and why the conversation founders avoid most is the one about splitting profits.

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Highlights From the Chat

Q: Why is it so rare for founders to talk about what went wrong?

Ugly Talk started when hustle culture was at its peak. It was about grinding hard. I was part of that. I went to many events and didn’t feel like I was learning much.

I felt very distant from the speakers because they made it look very easy: “I just raised this much money. I met the right guy at the right time.”

And I looked at what I do. I’m trying just as hard as you’re trying, and I’m going very slowly compared to what you’re doing. What am I missing here? When I talked to the rest of the audience, most of them had the same feeling.

Years ago, when I started a different company, an old wise man told me, learning from your mistakes is great, but you can learn from other people’s mistakes.

So, those two concepts came together. What if we invite people who have built amazing companies and brands, and they talk about how they messed up, what they learned and why they pivoted?

Q: You’ve heard thousands of ugly moments. What’s the most common one?

Misalignment of expectations, either between the two co-founders or within the founder themselves. Like, “I worked hard for three months, I’m going to get here,” and it just never works out.

The ugly moment comes through when people say, “I realized that was the wrong partner, because he came from corporate and I’m from tech.” Or there’s misalignment with family, with your spouse’s expectations.

So: ugly talk first, no pun intended. Be honest with yourself. Be honest with your other stakeholders. That’s a recurring theme in our talks.

Q: Which cities is Ugly Talk in now?

We started in Chicago, then quickly moved to New York, then Miami, Los Angeles and San Francisco. We’re trying to go international to London, Paris and Toronto.

But we want to democratize the brand so community organizers can host their own Ugly Talks. Our job is to empower them by giving them the tools, the logistics and the brand they need to have that conversation in their own community.

On the spot, Anson’s one-word take on each city’s founders: Chicago, down to earth. New York, hustle. Miami, flashy. Los Angeles, bougie. San Francisco, tech heavy.

Q: What’s a recent ugly moment from building Ugly Talk itself?

Misalignment again, with hosts and partners.

At a recent event there was a great turnout and really high energy. It looked amazing on social media. But from the brand’s perspective, they wanted a certain category of people and were seeing maybe 10% of them, while 90% were a demographic they don’t serve. They weren’t super happy, and we learned from that. Now we gather more information and are more transparent with the host and the brand.

Same with speakers. We weren’t preparing them well enough. Some came in expecting an assistant, maybe a private car, maybe lodging in other cities. We didn’t get to that part of the conversation until a week or two before the event.

That’s why you have a long SOP with very specific details. Somewhere in the past, somebody messed it up.

At one event, the producer forgot to hit record on the main camera. Is an SOP that says “make sure everything’s recording” boring? Yeah. But that’s how you run a business. We run so many events every month that we learn very quickly. We’re confident we’ve made probably 70% of the mistakes there are to make.

Q: How does Ugly Talk make money?

Right now revenue comes from two places: brand sponsors and licensing. We don’t make money off the founders attending. Ugly Talk has always been free, but curated and invite-only. If you match the demographic, we want you in that event.

Brand sponsorship is straightforward. If it’s the right audience for you, come in, tell everybody what you’re working on and maybe give an incentive to sign up for your product or service.

Licensing is what we’re testing this year. We licensed Ugly Talk to downtown Miami so they can have it in the city, which puts them on the map and creates energy to compete with places like San Francisco, New York and Chicago. We’re also exploring licensing to up-and-coming cities that want to be known for a certain topic, and to corporations that want to run internal Ugly Talks for employee knowledge sharing.

We run the event, but they control the topic and the audience. And because we have access to our whole subscriber ecosystem, a licensing brand can bring its own audience or have us curate one.

Q: If the world swings back to offline, why push Ugly Talk online?

I came from digital. When we saw AI coming in, we felt it could take a lot out of the content creation process and the content itself. That’s why we doubled down on in-person events. But there’s a scalability issue if you only do in-person events.

So we’ll still be in-person first, and the content will propagate on the internet. It’s more meaningful if you were there, but you can relive the experience, share it with friends and learn from a specific moment. We’re not going to be purely online. That’s not who we are. We start with the in-person experience, but we don’t stop there.

I like it when people are a little bit nervous at our events. They tense up, then they start relaxing, and that’s where the ugly moments come out. “Here’s how I messed up. Here’s what happened.” That is the magic.

Q: What’s your biggest productivity hack?

Scheduling emails. When I worked at a media advertising agency, I was very eager about replying. You email me at midnight, I reply in ten minutes. I’m that guy. But it isn’t sustainable, and people just expect you to keep doing it forever.

Scheduling emails was a game changer, because it set an expectation with clients: you’re not going to hear back from me over the weekend.

As a founder, you can’t help it. You see a problem, you want to solve it. So I still write the reply. I just schedule it.

Q: What’s the hardest lesson you’ve learned about building a team?

Delegating. I’m very close to the problem.

For an event, I care about the camera angle and the seating arrangement. You can’t delegate every single detail, so it was hard for me, especially with different cities. I didn’t see that I was micromanaging. It was my blind spot.

Then somebody told me, “Dude, why do you care so much? It’ll be fine.” And I was like, you know what, yeah, it will be fine.

I learned to let them do it their way, and a lot of hosts have risen to the occasion with events beyond my expectations.

Q: If you had a billboard in Times Square, what would it say?

Maybe on brand: “Ugly talk first.” Communicate the ugliest facts about starting a company to your partner and your co-founder first. Get the ugliness out.

As a culture, maybe Asian culture especially, we’re not very confrontational. We think maybe it’ll work out in the end. But usually that is the problem.

If I did it again, I’d rather say: here’s my flaw, here’s what I’m not good at, and here’s what I need from you. If it doesn’t work, it doesn’t work. But at least I’m an open book.

Q: What’s the conversation most founders avoid?

Splitting profits. I don’t know why people don’t want to talk about money. We’re in business, so you should be comfortable with money. But with partners and contractors, people leave the money part to the very end.

Then if you have very different expectations, like “I thought I was getting 30%,” and it’s 5%, you wasted an hour talking about everything else.

Money can get ugly, so talk about it first. Here’s the percentage, here’s how much we’re paying. Are we in the same range? Yes? Then let’s get into the details.

TIMESTAMPS

00:00 – Why “Ugly Talk” Exists (Founders Don’t Talk About Failure)

02:05 – How Ugly Talk Started

02:47 – The #1 Most Common “Ugly Moment”: Misaligned Expectations

03:47 – The Cities Ugly Talk Has Launched In

05:49 – A Recent Ugly Moment From Building the Business Itself

09:39 – How Ugly Talk Actually Makes Money (Sponsorships & Licensing)

12:40 – Will Events Go Digital, or Stay In-Person?

15:15 – Rapid Fire: Habits, Books & Productivity

20:41 – His Billboard Message: “Ugly Talk First”

22:15 – The Ugly Conversation Most Founders Avoid: Splitting Profits