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

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.

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)

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)

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

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.

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!