My First Million Live Event With Andrew Wilkinson (Austin, Texas) (Part 1)

Summary

My First Million: Live Event with Andrew Wilkinson (Austin, Texas) – Part 1

Date: May 12, 2023
Hosts: Sam Parr, Shaan Puri
Special Guest: Andrew Wilkinson

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Episode Overview

This episode of My First Million was recorded live in Austin, Texas, and features hosts Sam Parr and Shaan Puri alongside entrepreneur Andrew Wilkinson. The focus is on real, unusual, and sometimes wild business journeys — highlighting what it takes to build, acquire, and grow companies. The session includes live interactions with audience entrepreneurs, storytelling about close calls and missed exits, and candid discussions about the messy realities behind celebrated successes.

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Key Discussion Points & Insights

1. Kicking Off the Live Event (00:33–04:49)

• The hosts open with banter about the venue, poking fun at themselves and the “graduation party” vibe.
• They celebrate the eclectic nature of their audience and guests.
• Memorable moment: Playful apology and shoutout to the venue’s sound crew.
  • C: “Sound guys, sorry, but it is what it is.” (01:24)

2. The Art of Hosting and Nick Gray’s Legendary Improvisation (02:14–05:15)

• The hosts recount a rain-soaked dinner that was saved by friend and author Nick Gray, who orchestrated a last-minute venue change and kept spirits high.
• Nick is described as a "friend billionaire,” not in money, but in connections.
  • A: “Nick is a friend billionaire.” (02:37)
• Nick’s book, The 2-Hour Cocktail Party, gets a nod for its practical tips.

Notable Quote:

“He hosts this thing. What Nick does is he has this book called, I think, The Two Hour Cocktail Party. And he’s basically perfected the art of a two-hour party.”
— B (04:05)

• Nick’s resourcefulness is heroized, including running out in the rain to buy a sweatshirt for a cold guest.

3. Austin’s Unique Breed of Entrepreneurs (05:15–10:49)

• The dinner featured entrepreneurs with unconventional businesses:
  • Dog supplements company sold for $650 million.
  • Dog ramps business: $18 million/year.
  • Tractor marketplace and large car wash operator also introduced.
• Austin’s “weirder” entrepreneurial energy is contrasted with SF or NY.
  • B: “In Austin you get mustache, hat tilt... I’ll sell your dog some vitamins.” (06:37)
• Audience poll: Who owns businesses and their revenue ranges (07:08–07:38).

Live Q&A with Audience Entrepreneurs

• 365 Holdings (Kelsey Larrick): E-commerce roll-up; aspirations to “be Andrew Wilkinson.”
  • C: “I want to be Andrew Wilkinson when I grow up.” (07:56)
• Traction Capital (Justin Turner): Sells $37 million/year in fire department equipment. Profits revealed (10% margin), the value of exclusive distribution rights discussed (08:11–09:08).
• Koozie Printing: Runs a 40,000 sq.ft. print warehouse; first big win selling beer koozies online (09:28–09:55).
• Custom Dog Treats: Supplies branded treats to hospitality businesses like Ritz Carlton; reached $500K run rate in just 10 months (10:28–10:44).

Notable Quote:

“We make custom dog treats for hospitality businesses. So, like, when the Ritz Carlton has guests come with dogs, we provide the dog treats that they give to their guests.”
— Audience (10:28)

4. Andrew Wilkinson’s Near Misses and Building Tiny (11:01–15:38)

a. Building the Foundation

• Andrew created MetaLab, a digital agency, and used the profits to begin buying and investing in other companies, leading to the holding company Tiny.
• Tiny went public the previous week, now trading at $850 million CAD.

b. The Flow Misstep

• Andrew almost risked it all to launch a SaaS business called Flow, sending a late-night, beer-fueled message proposing to shutter MetaLab and focus entirely on the new venture.
  • A: “I got so excited... I sent this email to the entire staff and said, ‘guys, we’re shutting MetaLab down. We’re going all in on Flow.’” (13:03)
• Chris (cofounder/CFO) intervened, pointing out they’d be bankrupt in 3 months, and quietly reassured staff not to leave.

c. The Sale That Didn’t Happen

• Nearly sold MetaLab for $15 million about ten years prior. Signed paperwork, waited for wire — the deal collapsed because the private equity firm couldn’t close its fund.
  • A: “If the wire had come in, my business would be worth maybe nothing at this point... We almost lost it all.” (14:11)
• Now, MetaLab is likely worth hundreds of millions.

Notable Quote:

“Every business is a slow-motion knife fight... You just wake up in the morning, you’re sweating and you’re fighting, trying to survive.”
— A, quoting Brent Beshore (15:11)

5. Sam Parr’s “Almost Exit” to Vice (15:38–17:08)

• Sam describes feeling miserable during the grind of building The Hustle and almost selling it to Vice Media for $10 million in stock.
• At the last minute, he discovers Vice’s financial instability during a visit—everyone is in sexual harassment training; the deal would have left him with worthless equity.
  • C: “I almost took that because I was so, like, desperate to get out.” (16:53)
• The “close call” is a relief in hindsight—sometimes the best outcome is the deal you don’t do.

Notable Quote:

“The sexual harassment seminar almost saved you.” — B (17:04)

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Memorable Quotes & Highlights

• “Nick is a friend billionaire.” — A (02:37)
• “Every business is a slow-motion knife fight.” — A, quoting Brent Beshore (15:11)
• “We make custom dog treats for hospitality businesses... Ours have their branding on them.” — Audience (10:28–10:42)
• “I was just like, moment of insanity. And Chris went around to all the employees quietly and was like, ‘please don’t leave.’” — A (13:44)
• “If the wire had come in, my business would be worth maybe nothing at this point… So we almost lost it all.” — A (14:11)

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Timestamps for Significant Segments

• 00:33 – Event intro, venue jokes
• 02:14 – Nick Gray and the improvisational dinner save
• 05:15 – Austin’s unique businesses and roundtable sharing
• 07:43 – Audience entrepreneur introductions
• 11:01 – Story of MetaLab, Tiny, and the path to public listing
• 13:03 – The Flow near-disaster and Chris’s intervention
• 14:11 – The $15M missed sale
• 15:11 – "Slow-motion knife fight" and business anxiety
• 15:38 – Sam’s failed Vice Media exit

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Tone and Language

The conversation is casual, witty, and self-deprecating, peppered with playful banter among the hosts and guest, and candid exchanges with the audience. There’s an emphasis on real talk over glamour, highlighting the unpredictable, stressful, and sometimes absurd nature of entrepreneurship.

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For Listeners Who Missed It

This episode is especially valuable for entrepreneurs—or anyone interested in behind-the-scenes business struggles—who want the unvarnished truth about building successful companies. The stories span big wins, side-hustles-turned-empires, and major “what if?” moments. The audience Q&A adds further inspiration with its diversity of offbeat, profitable businesses.

Stay tuned for Part 2, including a live “Shark Tank” pitch session!

Transcript

[A]

And I got so excited about it at one point that I was up at like 11 o' clock at night. I was feeling all manic. I'd probably had a couple beers and I sent this email to the entire staff and I said, guys, we're shutting Metalab down. We're going all in on Flow and Chris, my business partner, who's here somewhere. Where's Chris? Chris over there. Chris was the CFO at the time. He looked at the numbers and he was like, we will be out of business in three months.

[B]

I feel like I can rule the world. I know I could be what I want to.

[A]

I put my all in it. Like a day off.

[B]

Keep standing.

[C]

Put your hands together for Webby, Award winning Sean Pury, Sam Par, and special guest Andrew Wilkinson. Come on out, you guys. Extra mics. All right, so we are. We are back stage and we saw like all the bands that have played here. It's like Franz Ferdinand and like the Killers and all these cool things. And I heard the sound guys. First of all, sound guys, I want to apologize. I heard them talking before this and they're like, what the fuck is this? Like, is this like a rich guy's birthday party? What is this?

[B]

I think they thought it was a graduation happening.

[C]

So sound guys, sorry, but it is what it is.

[B]

You always wanted to be a star. You wanted to walk out to a sold out venue and I guess this was. It's one way to do it.

[C]

Yeah, it's one way to do it. So, sound guy, it's going to be the lamest thing you're going to see this week, but maybe you'll learn something. I don't know, but this is awesome. What do you think?

[A]

Working?

[C]

Fuck you, sound guy.

[B]

Is this working?

[A]

Come on, guys, you can tell who.

[B]

The real podcasters are up here.

[C]

So.

[A]

So we did this huge event in Vancouver. We had like 1200 people in this massive theater. And Sam sneaks out on the stage and I'm like, what are you doing? And he's peering around the corner, taking photos, and he goes, I'm posting this on Facebook. And I was like, who the fuck uses Facebook? That's so weird. And he goes, all the people I went to high school with.

[C]

And so we wanted to start off by saying we were laughing backstage and we were like. Right before we came on, we were like, we gotta talk about Nick Gray. Does anyone here. Has anyone here met Nick Gray? That was the guy that was just talking.

[B]

I just met him for the first time last night. He is. I don't Know if he's the most interesting man in the world, but he's like the most interesting man in Texas for sure. I'll give him that.

[A]

I feel like on this show we always talk about billionaires, and there's a lot of money billionaires, but Nick is a friend. Billionaire.

[B]

Yeah. Last night. So we hosted a dinner last night with like, I don't know, 15 people. And Sam had set it all up. It was gonna be perfect. He had this, like, high end restaurant, table for 14. The time was locked in. We got reminders, we show up. It's supposed to be beautiful, you know, just a first class dinner. Everything was taken care of. And we get there, and immediately the plan was blown up. It was raining outside.

[C]

It starts raining like crazy. And our seat was like half outside.

[B]

Yeah. So we weren't gonna be able to do it. Immediately, Nick Gray improvises. He's like, hold on, you six to the bar. And then he sprinted. Because I pulled up, I saw him running. And I was like, nick, Ray, where you going? And he was like, I'm scoping out a venue. And he. I don't know where he went.

[C]

He runs into this place and he's like, hey, is this a event space?

[B]

And soaking wet.

[C]

Yeah. And the women look at each other and they're like, what? And he goes, what's the name of this place? And they go, it's called Miss Kitty's. And he's like, are you guys in event space? What do you do? He goes, we wax women.

[B]

Oh, I got 15 dudes outside. Do you have an event space or not? But he did. He found us this, like, abandoned shack, almost this amazing place. And he got us.

[C]

It was really like a shed.

[B]

It was an abandoned shed. But it was like. I don't know. It was perfect. It was exactly what we did. It was outside the rain. We were all in there. It was quiet, we could talk. And he hosts this thing. What Nick does is he has this book called, I think the Two Hour Cocktail Party. And he's basically perfected the art of a two hour party. And I got to see it firsthand. He takes out his harmonica to get everyone's attention. And then he has this way of getting everybody to open up, to talk, to sit in the right places, do the right things. And it was incredible. The best part, though, was he saved you.

[A]

So Nick is looking around, and he walks up to me. He goes, hey, are you all good? Everything good? And I say, okay, I want to go to the shed. I'm excited. I'm a little bit cold though. Is it going to be heated? And he goes, hold on, I'll be right back. And he runs outside and like Sam said, it's like pouring rain. I don't know if you guys witnessed this yesterday, but it was insane. He comes back, he's soaking wet. He looks like that scene in Glengarry Glen Ross when the guy's like at the doorstep and he brings me this sweatshirt which he had paid like $70 for. That's who Nick Gray is.

[C]

And the reason we're bringing this up is not because we like him, is.

[B]

To be clear, we like him.

[C]

To be clear, we like him. But that's not why we're bringing this up. But on our pod, my first million. And by the way, is everyone here. Is anyone who doesn't listen to MFM.

[B]

Here here for the graduation?

[C]

Yeah. Okay. And who here actually listens to us regularly? All right, that's good enough. And so we bring up all these like weird businesses that a lot of people haven't heard about. And this one is probably the weirdest one. He. He told me he was going to write this book about a cocktail party. I thought it was a horrible idea. And so far he's sold 11,000 copies of this book, which is insane. And he. And so we have this dinner and we meet all these interesting people at this like 14 person dinner. I think we had a guy there who sold a company that sold dog supplements, which is like the greatest business ever because who knows if it works, right? Like you have no idea. He sold his company for $650 million. It was insane. He was telling us a story about this. We had another guy who sells also dog related dog ramps. So like, so your old or small dog can like go up on the couch. And he does 18 million a year in sales. There was another guy there that has a website that is like a marketplace so you can rent a tractor and it's killing it. We had a person who has a, a bunch of. Owns a bunch of car washes that does tens of millions in profit. What else we have? Anything else? That was weird.

[B]

It was, it was crazy. It was different than San Francisco. If you go to San Francisco or New York, you get one type of entrepreneur. You get the AI crypto. You get that in sf. In New York you get something else. And in Austin you get mustache, hat, tilt. And like I sell tractors online or I'll sell your dog some vitamins. You know, you get a different type of entrepreneur. I bet in the, I bet in the Crowd right now, we got to have some interesting businesses.

[A]

Who here has a business? Let's get. Get a sense of who.

[B]

Get a hand up.

[A]

So keep your hand up if you own a business. And if you do over 100, raise them high.

[B]

Raise them.

[A]

Raise them like you're proud. If you do over $100,000, keep it up. If you do 500,000, keep it up. One million. Five million.

[B]

Okay, we got a few.

[A]

20 million. Anybody? No? Okay, back to five.

[B]

No, no, no. We got them over here. We got a couple.

[A]

Okay, 20 million. 20 million and up. Couple of.

[B]

We got one over here, two here, one in the back.

[A]

Any of those. Any of them profitable?

[C]

Okay.

[B]

All right.

[A]

Okay. Nick, we want to talk to these guys. I want to know what their businesses are.

[C]

Your hands up. Hand is up. I'm. All right. Stand up, please. Let's hear from you.

[B]

What's your name and what's your business?

[C]

Kelsey Larrick. 365 Holdings. We're an E. Commerce roll up.

[A]

Sorry, can you say that one more time? 365.

[B]

Slow motion, please.

[C]

365 Holdings. We roll up. E Commerce businesses. I want to be Andrew Wilkinson when I grow up.

[A]

You don't trust me?

[B]

He's blushing up here.

[A]

It's very sad.

[C]

It sounds like a good grade.

[B]

Who's the guy next to you?

[A]

Justin Turner. Traction Capital. We have a business that sells equipment to fire departments. What do you mean?

[B]

I love the way you said all that, but I'm gonna. Can I just try being you for a second? Sean Puri. Puri. Dad of. Dad of the house, change diapers. Like, you just said an awesome thing, but with such like. Yeah, you probably read about me. That's the vibe I got.

[A]

We sell, like, $37 million worth of equipment that fire departments use and firemen use every day.

[C]

Like. Like. Yeah.

[A]

Hoses, nozzles, uniforms. Uniforms. And why is. Okay, so. And what about competition? Is it just, like, you're the only one in town, there's only one place to buy them? Or do you have a moat of some kind? We have exclusive distribution relationships in nine of the Western states in the U.S.

[C]

How much profit on 37 million in revenue?

[A]

It's about 10% margin.

[C]

Does it feel uncomfortable when I ask you these questions? Should I ask, like, what do you look like naked? What was it like when you lost your virginity?

[A]

There's only one way to find out.

[C]

All right, what else? And who else?

[B]

Who's got a weirder story than that? Anybody got a weirder story? Yeah.

[A]

Put your hand up if you got a really weird business.

[B]

It was like, weird. Yes. Yeah.

[C]

Yeah. Hold on one second, please.

[A]

Hold on. Okay, so this is a paper koozie, but I own a 40,000 square foot print warehouse and we print real koozies. So, like, it's really niche and it's really random.

[B]

Not these small boy koozies that we handed out.

[A]

How long you've been running your business for? I've been in business for eight years, but we do a lot of different types of printing. Did you become a millionaire selling beer koozies? That was my first largest e comm store that I created.

[C]

Yeah.

[A]

Selling koozies because I'm from the Midwest and we drink a lot of beer and that.

[C]

You look like you're from the Midwest.

[A]

Yeah.

[C]

I just don't know you and I look.

[A]

I'm close to St. Louis, actually.

[B]

Is that your sister?

[A]

What's going on here?

[C]

Yeah, we can be cousins.

[A]

Anyone else have a really, really weird business? Like dog ramp level weird business.

[B]

Tell them to let the freak flag fly. Oh, here we go. Guy with the Austin stache.

[A]

There it is.

[C]

The capital V neck shirt.

[B]

You just grow those when you fly in. As soon as you cross the border, the mustache just pops up.

[A]

We make custom dog treats for hospitality businesses. So, like when the Ritz Carlton has guests come with dogs, we provide the dog treats that they give to their guests. And why wouldn't they just use normal dog treats? Because ours have their branding on them. Oh, very smart.

[C]

How big is that?

[A]

We started 10 months ago and we've grown it to half a million in 10 months at run rate. Wow, that's great.

[B]

This is cool. We're going to. We're going to hear more businesses because a little bit later we're going to do like a shark tank type of thing with a bunch of. Bunch of pitches.

[C]

Yeah, we can put the lights down two times.

[B]

Okay, there we go.

[C]

So the cool part about, like doing this stuff is we get to meet all these interesting people who are succeeding and some are failing, which is actually just. Or more interesting. But speaking of a big success, Andrew over here took his company.

[B]

I thought you were pointing at me.

[C]

Andrew over here just took his company public. It's called Tiny. It's not that tiny.

[B]

Yeah, that should be the tagline. It's not that tiny.

[C]

And you were telling. He was telling us a story that we had not heard about almost selling the company. Like six.

[B]

This was a backstage story. Can we tell it? I think we could.

[A]

Yeah, we can. We can tell it. So there's really two stories.

[C]

So one, by the way, if you don't know. I got to do the intro. Andrew started this thing called Metalab. It was an agency that made a bunch of tech stuff for big companies using the profits from that company. He then started buying and investing in other companies which. That hold company. That hold company, or holdco, was called Tiny. He recently took it public last week. It's now trading at 850 million Canadian dollars, which is only like 600 million bucks in real money. No, but it's a huge success. But it all started because he had this agency called Metalab, where he was, you know, like I said, doing stuff for tech people. But you were saying earlier that how that was like the foundation for the success of everything else. But you. It. You almost did something crazy early on.

[A]

Yeah, so I almost wasn't sitting. Wouldn't be sitting here. So we were sitting at dinner the other night and talking about this, and there's two stories. So one, I got very excited. You know, when you have a business, you always know how much it sucks, how hard it is to run, and you always admire other people's businesses. And so I always wanted, like a SaaS business, sexy business. And so I started one. I started this productivity business called Flow. It was like a sauna, except we didn't raise any money and we. We had a great product, but it just didn't go anywhere.

[C]

Like task management. Task management, which is one of the.

[A]

Hardest things, one of the hardest businesses in the world. And I got so excited about it at one point that I was up at like 11 o' clock at night. I was feeling all manic. I'd probably had a couple of beers and. And I sent this email to the entire staff and I said, guys, we're shutting Metalab down. We're going all in on Flow. And Chris, my business partner, who's here somewhere. Where's Chris? Chris over there. Chris was the CFO at the time, and he looked at the numbers and he was like, we will be out of business in three months.

[C]

How big was Flo?

[A]

Flo was doing like 300k of revenue and metal lab was 2 million or something like that.

[C]

And so how big was Metal Lab when you. When.

[A]

When you're 2 million maybe at that point.

[C]

So 2 million in revenue versus 300,000.

[A]

300K or something. I was just like, moment of insanity. And Chris went around to all the employees quietly and was like, please don't leave. Please don't leave. We'll be bankrupt in like a week. And save the day. And then the second story was Chris and I, we, you know, running an agency is really stressful. And we got this offer for the business to sell it for 15 million. This is about eight or nine years ago, almost 10 years ago.

[C]

And 15, 1 5.

[A]

151 5. And we actually went through the whole process, you know, spent four months going back and forth with this private equity firm. We signed the documents. You know, my lawyer calls me in quivering hand. I signed sign the documents. And the wire's supposed to come in the next day. And so I wake up, I go to my local bank branch, I go to the ATM and I look at the balance. My balance is the same. And I think, okay, it's probably going to come in later. So I check later, nothing. Next day, nothing. Next day, nothing. I call the guy at the private equity firm and he goes, hey, man, I'm really sorry, but we weren't able to finish closing our fund, so the deal is not done. So I legally sold the business. And if the wire had come in, my business would be worth maybe nothing at this point because this was the entire foundation of the business and we would be tiny. So we almost lost it all.

[C]

What do you think it's worth now, Metalab?

[A]

I don't know. Hundreds of millions for sure, but I don't know.

[B]

It all could have just one decision. Actually, you made the decision.

[A]

And it was all driven by anxiety, right? It's panic. I'm sure every one of you that runs a business, everyone knows how miserable it is inside, right? You talk to people, you look at them on the outside, you go, they're an amazing operator. They have a great business. But on the inside, there's a great quote by Brent B. Sure. He goes, every business is a slow motion knife fight, right? Like, you just wake up in the morning, you're sweating and you're fighting, trying to survive, right? And we felt that way and we pushed through and it was okay, but we almost gave in.

[B]

Did you. Before you sold the Hustle to HubSpot, did you ever almost. Did you come close to selling before that?

[C]

So when I was running the company, I was miserable most every time. So if you go on like Facebook or Instagram, look at my Pictures from like 2017 and 18, I was lumpy. I was like, pretty fat. And I was like. Cause I was eating all the time to make myself feel better. So I was miserable most of the time. And then this one company emailed me to. They showed interest in buying. And so I fly all the way out to New York. And I start talking to them, and I get in their office and, like, it's empty. And I'm like, where is everyone? And they're like, oh, they're doing stuff. And they take me to an office to have the meeting and. And I look in the windows of each office, and they're in a. Every employee is in a sexual harassment seminar because the CMO had just, like, you know, gone off the rails and did a bunch of bad shit. And so they get me in a room, they, like, send me a term sheet, and they're like, well, buy your company for $10 million, but it's going to be all in stock. And I was like, well, show me the financials and, like, let me see what's going on with your business. And I got a peek in it, and the company was Vice, Vice Media, which means that deal, I was so close to taking it, it would be worth zero. I'd probably be in debt because Vice, like, the valuation has just plummeted. And so I almost took that because I was so, like, desperate to get out.

[B]

The sexual harassment seminar almost saved you.

[C]

It did. Yeah. Yes.

[B]

You're a survivor. I feel like I can rule the world.

[A]

I know I could be what I want to.

[C]

I put my all in it.

[A]

Like, no days off on the road.

[C]

Let'S travel, never looking back.

[B]

Hey, let's take a quick break because there's a quote that I love, I want to read you. It's that we shape our tools, and thereafter, they shape us. And, you know, as an entrepreneur, if you're using a bank that was built in the 90s, you're operating like you're in the 90s. And trust me, I've been there. Clunky portals, right? Random holds on your money, $50 wire fees, and then being told, please visit your local branch. Well, that's why I switch to a different type of banking solution, Mercury. It turns your financial chores into a smooth workflow. You can do wires, invoices, cards, reimbursements. Two clicks and I'm done. If you're already using Mercury, respect. If you're still using one of the old big banks. I got questions for you. So go visit mercury.com and give it a test drive. Mercury is a financial technology company, not a bank. Banking services are provided through Choice Financial Group, Column A and Evolve bank and Trust Members FD.