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Jan 8, 2024 · 20m · founders-journal

I Did Something Crazy

Alex Lieberman · 18m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Alex Lieberman breaks down how he secured $35,000 worth of 50-yard line College Football National Championship tickets fully funded by HubSpot in exchange for a live guerrilla marketing stunt. Across the episode, he details the deal's rapid negotiation, the 'HubSpotted' campaign mechanics, and key entrepreneurial lessons on taking asymmetric bets and building brand momentum.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 99.9% of the talking time here. How this is scored →

Alex as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.0 Alex pushing back 0.0
05100:0010:0020:001:56–6:49 · Alex as informed peer 0/10 The Michigan Semifinal Win and the StubHub Ticket Dilemma Alex delivers a solo storytelling monologue about Michigan's playoff win and pitching brands on Twitter to fund national championship tickets. There is no active guest dialogue or debate.6:49–11:10 · Alex as informed peer 0/10 The Dude Wipes Proposal and Initial Rejection Alex continues his monologue detailing the interaction with Dude Wipes' CEO and the incoming corporate sponsorship offers, without any conversational sparring.11:10–16:31 · Alex as informed peer 0/10 HubSpot Creative Strategy and Setting Success Metrics Alex discusses the brainstorm session with HubSpot and developing the 'HubSpotted' live Where's Waldo concept in a solo narrative format.16:32–17:43 · Alex as informed peer 0/10 Applying the Hub and Spoke Model to Live Events Alex wraps up his solo monologue by explaining how live sporting events fit into a hub-and-spoke audience acquisition model.1:56–6:49 · Guest teaching 0/10 The Michigan Semifinal Win and the StubHub Ticket Dilemma Alex delivers a solo storytelling monologue about Michigan's playoff win and pitching brands on Twitter to fund national championship tickets. There is no active guest dialogue or debate.6:49–11:10 · Guest teaching 0/10 The Dude Wipes Proposal and Initial Rejection Alex continues his monologue detailing the interaction with Dude Wipes' CEO and the incoming corporate sponsorship offers, without any conversational sparring.11:10–16:31 · Guest teaching 0/10 HubSpot Creative Strategy and Setting Success Metrics Alex discusses the brainstorm session with HubSpot and developing the 'HubSpotted' live Where's Waldo concept in a solo narrative format.16:32–17:43 · Guest teaching 0/10 Applying the Hub and Spoke Model to Live Events Alex wraps up his solo monologue by explaining how live sporting events fit into a hub-and-spoke audience acquisition model.1:56–6:49 · Guest disagreement 0/10 The Michigan Semifinal Win and the StubHub Ticket Dilemma Alex delivers a solo storytelling monologue about Michigan's playoff win and pitching brands on Twitter to fund national championship tickets. There is no active guest dialogue or debate.6:49–11:10 · Guest disagreement 0/10 The Dude Wipes Proposal and Initial Rejection Alex continues his monologue detailing the interaction with Dude Wipes' CEO and the incoming corporate sponsorship offers, without any conversational sparring.11:10–16:31 · Guest disagreement 0/10 HubSpot Creative Strategy and Setting Success Metrics Alex discusses the brainstorm session with HubSpot and developing the 'HubSpotted' live Where's Waldo concept in a solo narrative format.16:32–17:43 · Guest disagreement 0/10 Applying the Hub and Spoke Model to Live Events Alex wraps up his solo monologue by explaining how live sporting events fit into a hub-and-spoke audience acquisition model.1:56–6:49 · Alex pushing back 0/10 The Michigan Semifinal Win and the StubHub Ticket Dilemma Alex delivers a solo storytelling monologue about Michigan's playoff win and pitching brands on Twitter to fund national championship tickets. There is no active guest dialogue or debate.6:49–11:10 · Alex pushing back 0/10 The Dude Wipes Proposal and Initial Rejection Alex continues his monologue detailing the interaction with Dude Wipes' CEO and the incoming corporate sponsorship offers, without any conversational sparring.11:10–16:31 · Alex pushing back 0/10 HubSpot Creative Strategy and Setting Success Metrics Alex discusses the brainstorm session with HubSpot and developing the 'HubSpotted' live Where's Waldo concept in a solo narrative format.16:32–17:43 · Alex pushing back 0/10 Applying the Hub and Spoke Model to Live Events Alex wraps up his solo monologue by explaining how live sporting events fit into a hub-and-spoke audience acquisition model.

speaking balance: gold is Alex, purple is the guest (3 minute bins)

0:00 · Alex 100% · guest 0%0:00 · Alex 100% · guest 0%3:00 · Alex 99.8% · guest 0.2%3:00 · Alex 99.8% · guest 0.2%6:00 · Alex 100% · guest 0%6:00 · Alex 100% · guest 0%9:00 · Alex 100% · guest 0%9:00 · Alex 100% · guest 0%12:00 · Alex 100% · guest 0%12:00 · Alex 100% · guest 0%15:00 · Alex 99.8% · guest 0.2%15:00 · Alex 99.8% · guest 0.2%18:00 · Alex 100% · guest 0%18:00 · Alex 100% · guest 0%
Sharpest disagreement ▶ 4:08 No combativeness present in solo monologue

The episode is entirely a solo host narrative, with no opposing guest or contentious exchange.

 Hardest push from Alex ▶ 7:00 Host describes Dude Wipes rejection

As a solo episode with no guest to challenge, the host only describes external negotiations where a brand turned down a timeline.

 Biggest teaching moment ▶ 11:50 HubSpot team defines success criteria

Alex recounts HubSpot's marketing team outlining the exact three metrics that would define a win for their campaign.

 Alex holds their own ▶ 16:32 Alex details the hub-and-spoke marketing model

Alex demonstrates marketing framework expertise by breaking down how massive live events act as customer acquisition hubs.
the scores for every segment, with the reasoning behind each
ChapterTopicAlex as informed peerGuest teachingGuest disagreementAlex pushing backWhy
The Michigan Semifinal Win and the StubHub Ticket Dilemma 0000 Alex delivers a solo storytelling monologue about Michigan's playoff win and pitching brands on Twitter to fund national championship tickets. There is no active guest dialogue or debate.
The Dude Wipes Proposal and Initial Rejection 0000 Alex continues his monologue detailing the interaction with Dude Wipes' CEO and the incoming corporate sponsorship offers, without any conversational sparring.
HubSpot Creative Strategy and Setting Success Metrics 0000 Alex discusses the brainstorm session with HubSpot and developing the 'HubSpotted' live Where's Waldo concept in a solo narrative format.
Applying the Hub and Spoke Model to Live Events 0000 Alex wraps up his solo monologue by explaining how live sporting events fit into a hub-and-spoke audience acquisition model.

Statements from this episode (9)

Disclosure
HubSpot funded 8 50-yard line National Championship seats for a guerrilla stunt
“Eight of us are being sent to this game. We'll be sitting in some of the best seats in the house at the 50 yard line. We will be in these seats for free. We did not pay a dollar for these seats. The reason is HubSpot, a twenty seven billion dollar publicly tra…”
Alex Lieberman Jan 8, 2024 ▶ 1:03
Assertion Not checkable as stated
Alex Lieberman's brand sponsor pitch tweet generated over 1 million total views
“That tweet ended up getting 537,000 views on Twitter. I think it got another 500,000 views on LinkedIn.”
Alex Lieberman Jan 8, 2024 ▶ 5:50
Insight
Cold outreach and public pitches are rare asymmetric bets with zero downside
“I believe there are so few examples in life where you can take riskless bets, meaning when you can do something that has a ton of asymmetric upside, meaning like something really cool could come out of the thing you're doing, but there is zero downside. And fi…”
Alex Lieberman Jan 8, 2024 ▶ 6:05
Assertion Not checkable as stated
Dude Wipes passed on $35k championship game stunt over timing constraints
“An hour later, the CEO of Dude Wipes followed up, and it was a no-go. He basically said his creative team thought it was a really good idea, but they did not think there was enough time left until the game to actually put something together.”
Alex Lieberman Jan 8, 2024 ▶ 7:56
Insight
A willingness to be cringe and shameless is an entrepreneurial superpower
“Being willing to do things that are cringe and shameless is actually one of the biggest superpowers of an entrepreneur. Because when you're willing to do things that other people won't do because they have fear of embarrassment or rejection, it gives you the o…”
Alex Lieberman Jan 8, 2024 ▶ 10:07
Prediction Not checkable as stated
HubSpot's $30,000 stunt was expected to generate multiples in earned media
“And by the way, I was confident from the beginning that we could get multiples of. 30,000 dollars in terms of earned media and impressions for the brand.”
Alex Lieberman Jan 8, 2024 ▶ 11:22
Assertion Not checkable as stated
HubSpot defined sponsorship success as virality, national TV, or press coverage
“And what they basically said to me was there are three things that if we get any of these things, We've knocked the cover off the ball. We've gone viral on social media. You've been spotted on live national television, or a journalist, especially of like a mar…”
Alex Lieberman Jan 8, 2024 ▶ 12:39
Insight
Live sporting events are perfect distribution hubs to reach millions of viewers
“And I think a sports stadium or a live sporting event Is the perfect example of a hub, which is, it's a singular place that has access to millions of people. You have access to the tens of thousands that are in the stadium, and then the tens of millions that a…”
Alex Lieberman Jan 8, 2024 ▶ 16:56
Insight
Content storytelling is one of the best ways to build startup momentum
“One of the best ways to build a company is to create momentum around your company. And one of the best ways to create momentum around your company Is to create content around your company so people feel like they are along for the ride, for the journey, where …”
Alex Lieberman Jan 8, 2024 ▶ 18:11
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