State of Play

This founder set an expiration ate for his company… and then hit 0M ARR.

Eric Simons (the builder behind Bolt.new) turned “we’re shutting down” into the world’s largest hackathon.

In this episode, we break down Eric’s probability playbook and how I’m applying it on my 60‑day clock to keep State of Play alive beyond October 1st.

We talk last bets, 100 swings, hackathons that print customers, and the automations I'm using to help me keep swinging.

WHAT YOU'LL LEARN:
- How an "end date” forces focus (and why it worked for Eric Simons)
- The 100‑swing probability game for finding PMF again
- Turning ideas into sales leads (not “projects”)
- A real automation stack: Polar → n8n → Notion → email for code fulfillment
- Why designers are becoming builders and what that unlocks

SUPPORT THE SHOW:

UX Tools Newsletter (written by me):
Join 100,000+ designers for weekly insights → https://uxtools.co

CHAPTERS
00:00 – “In 60 days, it’s over” (cold open)
00:16 – Meet Eric Simons + the 0M ARR plot twist
00:30 – The decade everyone ignores (failure before the hockey stick)
02:30 – The Dropout DNA (living in an office, working 6am–3am)
03:30 – The 0,000 reality check vs a 00 Bolt build
05:00 – The Probability Playbook: take 100 swings
07:00 – The office‑squatter strategy (desperation, channeled)
09:00 – The competitor’s funeral + picking a death date
11:00 – The builder uprising
11:45 – The million‑dollar tweet (how the hackathon started)
13:00 – Meet the 100,000 (designers → builders)
15:00 – The only title I wear
16:00 – The last swing (countdown to Oct 1, 2025)

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Eric: https://x.com/EricSimons
Try Bolt: https://bolt.new

FOLLOW ME:
YouTube: https://youtube.com/@designertom
Instagram: https://instagram.com/itsdesignertom
X / Twitter: https://x.com/designertom
LinkedIn: https://linkedin.com/in/tommygeoco

What is State of Play?

Conversations with designers, founders, and builders behind some of the best work

Final Assembly - Ep 3.txt
English (US)

00:00:00.000 — 00:00:19.840 · Speaker 1
In 60 days. I need to tell my team. We're done. Cancel the shoots, return the equipment, admit that maybe I'm just another failed founder with a podcast. If I don't make $50,000 by October 1st, this all goes away. But then I met the guy who gave his company 30 days to live. What happened next would make him $40 million.

00:00:19.840 — 00:00:33.520 · Speaker 2
We're going to shut down the company at the end of the year. So between now and then, whatever cool ideas we think we have on how to use this technology like new product types, let's launch them because this is it. Like and that is where bolt came from.

00:00:33.520 — 00:00:36.160 · Speaker 1
Was bolt was your last swing?

00:00:36.280 — 00:00:40.640 · Speaker 2
It was the last swing. We were we were going to begin shutting down the company. A month after we had launched.

00:00:40.640 — 00:00:45.320 · Speaker 1
Bolt, he turned certain death into the world's largest hackathon. Here's how.

00:00:47.560 — 00:00:48.440 · Speaker 1
I'm swinging it.

00:00:48.440 — 00:00:52.440 · Speaker 2
Everything was the first time in history you're actually going to just build something.

00:00:52.920 — 00:01:00.120 · Speaker 1
Everyone talks about hockey stick growth, but no one talks about the decade of failure. That comes first.

00:01:00.160 — 00:02:06.080 · Speaker 2
It's kind of like Dropbox before Dropbox. A Dropbox is a hell of a lot more than what I'm about to describe, by the way. Like the the problem being like when you would go to school back then, it was like you had the USB flash drive, so you can like, do your schoolwork and load on the USB flash drive, bring it to school, bring it on.

But if you forgot it at home, a lot of teachers would just like you, give you an F for whatever they're like. You know, if actually you didn't do the work, if you didn't bring this thing, it's kind of a pain in the butt. Albert actually had the idea for the thing, and he was like, let's create a site. Forget the drive.

Com that's what it was called. And basically you can upload your files there and you can go between there and school and you have to bring a USB flash drive and blew people's minds. It was even after we left high school, you know, 2010, 2011, people were using it like 4 or 5 years after. This was like, what at that point is like Google Drive is now, you know, Microsoft has something, you know, like everything's out.

But, um, but it was kind of funny, but it was like they kind of took over that at that region of Illinois was like that. It was like the tool that like people were using, like store files. And that was that was cool because it was like, okay, wow. So you can actually just have an idea, go and implement it. And, and then people use this thing that's like, unbelievable.

00:02:06.120 — 00:02:13.240 · Speaker 1
Eric built Dropbox before Dropbox at age 13, but then nothing worked for a decade.

00:02:13.240 — 00:02:31.920 · Speaker 2
I think there's a lot more in common with your with you. And I honestly, because I think, you know what what we found was forget the drive. Most of the things we tried after now is probably 2008, maybe. Are you 7 or 8 or something like that? We spent pretty much a decade after that just striking out.

00:02:31.920 — 00:03:01.560 · Speaker 1
I know this feeling. In 2015, my startup caught fire and I woke up to this tweet from a popular streamer and then another one. And within a week we had 100,000 daily active users, not monthly daily. This was product market fit and I'd never felt anything like it. But then I sold it. Not because I wanted to, but because I was broke.

I've always wondered if that was my last shot. It took Eric a lot of grit to ever feel that feeling again.

00:03:01.600 — 00:03:50.840 · Speaker 2
I came out here when I was like 18 or 19, and I said that here is Silicon Valley and I'm originally from the Midwest. I grew up in a suburb, Chicago. Coming out here, I was like, I was broke. I wanted to, you know, build businesses and build startups and, you know, build great products. And so I found my way out here, um, you know, raised like 20 K for, like one of these accelerators.

And then, and, you know, in Silicon Valley that goes, you know, through in like months. Once I ran out of money, I was like, okay, I'm, you know, 19, uh, so my, my, my bar for, you know, standard of living is pretty low. And uh, I was like, you know, like they had, like, couches at that office building, a guy, you know, like a shower and the gym, they have ramen that's like, you know, stocked and stuff.

And so I was like, yeah, like, I could probably just, like, live out of here for, like, you know, a couple days or a week or something. And then that turned into like four months or five months until they finally caught me and they kicked me out.

00:03:50.880 — 00:04:17.640 · Speaker 1
He squatted at AOL for months. Meanwhile, I'm over here in a Home Office study contractors playing it safe while losing $8,000 per month. And my daughter was just born three weeks early. Healthy. I'm over the moon. But I did foolishly think I had a little more time to get projects out the door. Instead, I'm getting some work done in between 3 a.m. feedings.

00:04:17.680 — 00:04:36.360 · Speaker 2
A lot of the folks that will do this that got quotes from agencies before trying bolt the cost reductions, like 99%, like literally. So there was a guy who built a CRM. Um, there was like an AI powered CRM, had an agency called him 30 Grand, and he built it in bolt for 300 bucks, and they said it was going to take six months.

He had it done in three weeks.

00:04:36.600 — 00:04:37.160 · Speaker 1
Wow.

00:04:37.360 — 00:04:40.320 · Speaker 2
And he's not he's not a developer. Like he's not a he's not a software developer.

00:04:40.640 — 00:05:26.930 · Speaker 1
I've invested $60,000 this year alone, building the traditional way, hiring contractors, following mostly conventional wisdom. But if I can't figure out a path to sustainable revenue, I'm going to have to make some changes. Which brings me to this. If you are feeling the itch to start building, I want to tell you about something I put together for you.

And it was not easy. I partnered with tools that are shaping the future of product and design work. This is the UX Tools Bundle $129. One time gets you access to over $9,000 of premium features for the rest of this year, but only to the first 1000 that sign up. It also ends September 1st of 2025, so visit UX tools Co to jump into this bundle while it lasts.

Thanks for supporting the show. This is how we keep it moving.

00:05:26.930 — 00:07:33.490 · Speaker 2
Really to me. I've learned about entrepreneurship and being an entrepreneur is that if you go and read it, articles in the media or whatever, there's like you, oh, this visionary person had this visionary idea and like, that's what made it successful. Whatever. Right. So there's kind of like, okay, well, I guess I could be a visionary.

I could have a visionary idea, and therefore I will be successful. That's really that's like, not at all how it works. Like, what it really is, is and I should say, like, of course there are visionary people that have visionary ideas at the right place and time, with the right knowledge and skills to be able to execute on it.

And that's the huge asterisk around it, is that, um, to be at the right place in time, with the right knowledge and skills is it's a probability game. And so if anyone's ever worked in like sales, you want to sell $1 million or something or whatever, the way that you would break down your sales pipeline is like you're going to have, like, you know, maybe 100, you know, cold calls that you do have those maybe ten turn into warm leads of those, you know, maybe three convert.

And then that's like how you get to $1 million or something like that. Right? But it's a complete probability game, of which most of the things that you do and the people you talk to and the ideas you have, it don't matter and go away. But it doesn't matter, because as long as you turn over every stone like probabilities, you know of the funnel, you will go and close deals.

Same thing applies to entrepreneurship and building businesses. It's purely a game of like how many hits it bat can you get? How many, how many product ideas, how many iterations on those products? Like how fast can you take an idea, put it into the world, get feedback on it, iterate, rinse and repeat. Because there's really there's only two things that are going to happen.

One is that it's going to work to some degree, whether it's small or large or whatever, and that's great. It's like, okay, well, let's go and double down and iterate more or it's not. And then you get to go and get feedback of why doesn't this work? Like, should I go and iterate on it? Or should I kind of build a different thing that's based on this thing that people are saying is important or whatever, right?

Or should I just like, put that on the shelf? Try out a different idea completely. And so the thing is, that's kind of the fun of it, is that you have no idea going into any of these. Like when we launched bolt, we had no idea like that it was going to explode in the way that it did. And so that's, it's it's all about like showing up, like putting in your best work and, and you never know what's going to happen.

00:07:33.650 — 00:09:17.530 · Speaker 1
Eric talks about taking 100 swings. And I'm not precious about any single project anymore. I'm swinging at everything. Like internet enjoys trying to produce media about creative tech that my teenagers would watch, get inspired by, maybe learn from, or UX tools. Building the insider pulse on design tools through surveys.

Awards, newsletters and now memberships or even lore. Light my DND app, which might become a business, might not, but it's how we're sharpening our steel. These are my bets, my big swings, my version of Eric's probability game, and one of the ways I'm able to maintain so many swings is through AI tools and automation.

But not for shipping software. Not yet, but for eliminating busywork. Watch this. So my UX tools bundle gives people access to premium plans of a bunch of modern tools. But here's the problem I have 1000 unique codes per tool. That's almost 10,000 promo codes to distribute to individual customers, and doing this manually would be an absolute nightmare.

So I built a workflow in an automation tool called Nan. This is not sponsored. I just thought you'd like to see how I do this. Here's how it works. The purchase hits polars. This triggers the workflow in N18, which then queries the database in notion for the next available code package. It assigns them, logs the status so they don't get reused, and then it sends the customer the email and I just set and forget this.

This probably saved me 40 hours of building and maintaining all the support requests for this bundle. That's 40 hours I can continue spending on other swings.

00:09:17.610 — 00:09:32.010 · Speaker 2
I was working from, you know, six in the morning until, you know, 2 or 3 in the morning. It was I was I was just, you know, coding nonstop on my first startup. It was just, you know, that that pure, you know, entrepreneurial drive, you know, that kept me doing that.

00:09:32.050 — 00:09:50.530 · Speaker 1
I remember this time at one of my many failed startups, one of my co-founders got a job at a dispensary, not for the money, but because we wanted to understand their inventory problems firsthand. That is how desperate we were to solve the problem. Eric was desperate to. He just channeled it a little differently.

00:09:50.570 — 00:10:11.650 · Speaker 2
And you know, what worked is when we said we're like, all right, that's not working. Last year this was that shit hasn't worked for the past couple years. We've done it. We're going to shut down the company at the end of the year. So between now and then, whatever cool ideas we think we have on how to use this technology like new product types, let's launch them because this is it.

Like and that is where bolt came from.

00:10:11.650 — 00:10:14.290 · Speaker 1
Was bolt was your last swing?

00:10:14.410 — 00:10:20.050 · Speaker 2
It was the last swing. We were we were going to begin shutting down the company a month after we had launched October 1st.

00:10:20.050 — 00:10:36.410 · Speaker 1
That's the date either UX tool saves us or I defund the projects. Eric gave himself 30 days. In fact, one of his competitors at the time shut down two weeks before bolt was launched. They both chose the same strategy to shut down, but only one of them was reborn.

00:10:36.450 — 00:12:50.570 · Speaker 2
The direct competitors behind one of our most direct competitors shut down two weeks before we launched bold, because that is what they did. The whole hackathon idea, too, wasn't even our idea because this guy KP, who I now know and he's an amazing guy. Super nice, brilliant guy. He works in girls over at pal.

I think he was. He tweeted this idea. He was like, you know, if I, if I'm, if I was the CEO of bolt, like what I would do is throw the world's largest hackathon, have Guinness World Records certified as the largest hackathon, and have everyone come and build apps with bolt. Because this is the first time in history you could have a hackathon that's not just developers, right?

So you could have literally the biggest hackathon that could have ever happened in history. Right now, do it on bold and, you know, uh, have the results be live stream, etc. it'll be the biggest marketing event of the year. And so I replied and I was like, all right, let's do it. And then and then the whole thing went viral because I quote tweet.

And I was like, okay, so like, if we're gonna set a world record, we need to, you know, have a big prize like maybe 100 K. And then within a couple of hours we had a million, you know, verbally secured, you know, for the thing. And it just it just turned into this whole viral spectacle of just like, you can just do things.

This guy tweeted a thing. We were like, let's do it. And then all these other companies poured in to to be a part of it. So I think that's kind of cool because I think if you look at a typical company, they would not be yellowing $1 million hackathon. Uh, especially like now that we know what it takes to run one of these.

I mean, you know, like we're it's it is a lot. It's a lot to do, especially at this scale. No one's done it this scale before. Right. So like it's a lot of work. But you know, any other company would be like, uh, red tape, like. Oh, no, like the million things that can go wrong. And like, is this actually the best thing we can do?

Yeah, we have fun with that. Um, like, The Chainsmokers are investors of ours. And so, um, you know, when they got got word of, they were like, hey, you know, what could we do? And they're like, we could pop out a concert. And so that was this thing got kicked off with the Chainsmokers concert, um, that we had a whole bunch of people come out to and stuff.

So we like to lean into things that that are just organic and and just like, you know, cool and and and genuine and, uh, yeah, they're going to be really high impact, which I think is exactly. This is like, it's so cool. This has been a fun one because it was like in Q1 road mapping. This was not on the Q at the Q2 roadmap.

You know, but it just it popped up and we're like, we're doing this.

00:12:50.610 — 00:13:17.330 · Speaker 1
He went from this death date to $1 million hackathon, all thanks to one tweet. No planning. Just we're doing this. And that's the same energy I'm bringing to the UX tools bundle and negotiated with my favorite companies. $9,000 of software value for $129. If this thing sells out, that's $129,000 we can spend to pay the team, fund our projects, continue swinging for soul.

But if it doesn't do.

00:13:17.330 — 00:13:52.660 · Speaker 2
Fast forward five years. What I would really love to see happening is more entrepreneurs building businesses on the internet, like making their first dollar via a through ball, right? Like be a launching stores or SaaS businesses or whatever have you. And I would love to see more people that work, maybe even work on products today, but are actually like building them.

So like designers or PMS, instead of just making a JIRA ticket, they're actually going to bolt and they just hit enter and it just does it and they're crafting the product themselves. And if folks have, you know, ever had an idea for an app or a website or whatever, this is the first time in history you can actually go and just build something.

00:13:52.660 — 00:14:59.900 · Speaker 1
I talked to designers daily who are having these identity crises bouncing between coding and automation and marketing, starting their own businesses. And they tell me this traditional title designer is feeling less and less suitable to them. In fact, more and more designers are bending tools to get things done in nontraditional ways.

Like Brett Williams, who is famous for running seven figure design agencies like design Joy and Seventh Form as a one man operation. Side note many are very skeptical about how Brett does this, so I'm going to follow him around with the camera for a day and reveal his entire process. Stay tuned. And then there's Andy Allen, who leaves digital and uses things like 3D printing, Legos, and other physical metaphors to explore ideas for his line of not boring products.

or Marissa Sensical, who's using AI tools like Cursor or Figma make to bring many of her charming apps to life, like her yearbook or photo booth, or even her Tai language learning app. I told Eric the only title that resonates is dropout, but there might be a better one.

00:14:59.940 — 00:15:33.100 · Speaker 2
Five years from now, it's like you should be able to build, you know, very complicated by software and applications without needing to know how to code at all. That, to me, is what I would hope to see, will hope to see happen, and I would hope to see that reflected in how companies. Org chart twisted up like having where designers and PMS are more empowered than ever to actually go and, you know, really craft the product not just in Figma but actually in in the actual output app itself.

00:15:33.140 — 00:16:00.819 · Speaker 1
We are internet employers, the ones who learn HTML to edit our Neopets pages or pirate Photoshop at age 13. We consume to create. Not to criticize. We don't create for algorithms or VCs. We create because we can't not create. And because the internet is still magic. When you strip away the metrics and the reply, guys!

AI isn't killing creativity, it's just waking us up to it. Eric had 30 days. I've got 60

00:16:01.940 — 00:16:03.700 · Speaker 1
and she came early.

00:16:07.140 — 00:16:13.900 · Speaker 1
I had this whole plan. Launch two shows. Ship an MVP. Secure the partnerships.

00:16:15.140 — 00:16:16.940 · Speaker 1
Just in time for her birthday.

00:16:18.500 — 00:16:20.180 · Speaker 1
But she had other plans.

00:16:22.420 — 00:16:30.220 · Speaker 1
Now I'm writing scripts with one hand while she sleeps in the other. Recording episodes in between feedings.

00:16:34.620 — 00:16:39.820 · Speaker 1
You know what's messed up? This countdown, this pressure.

00:16:41.460 — 00:16:42.700 · Speaker 1
It makes me better.

00:16:43.900 — 00:16:47.100 · Speaker 1
Faster. A little more focused.

00:16:50.140 — 00:17:23.980 · Speaker 2
Build cool, fun stuff that you want to use to solve your own problems. And and be patient. Because, like, it takes time, you know? And, uh, you have to, you know, you have to explore every nook and cranny. Like when you're building a business, it's never like this straight line of success. There's always all these, you know, these these side paths you have to go down to, like, go and explore and whatever have you.

And, and the journey is long. And so it's just being patient and like, you know, having grit and sticking through it. And that is where Stack Foot started. That is where bolt started. That's where I forgot the drive started. All the stuff that's ever worked, you know it starts there.

00:17:24.100 — 00:17:30.460 · Speaker 1
Follow me on YouTube. As I learned to build this thing from some of the best in the business.

00:17:31.900 — 00:17:33.220 · Speaker 1
I'll see you next time.