Mar 28, 2023 · 1h 1m · founders-journal
The Business Behind Conferences + Embracing Confrontation
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 and Jesse Pujji analyze the lucrative business model behind major conferences, master management candor, and explore the psychological resilience needed to navigate startup volatility. They provide actionable frameworks for organizational culture, conference ROI, and deciding when to pivot or shut down a venture.
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 46.4% of the talking time here. How this is scored →
Alex as informed peer 4.5 Guest teaching 3.6 Guest disagreement 1.6 Alex pushing back 1.9
speaking balance: gold is Alex, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 38:14 Defending in-person conference velocity
Jesse firmly counters Alex's assertion that meetings can be replicated digitally by pointing out the irreplaceable speed and density of meeting thousands of leaders face-to-face.
Hardest push from Alex ▶ 38:07 Pushing on conference ROI vs remote outreachAlex challenges Jesse's rationale for traveling to conferences by pressing whether those same 25 meetings couldn't be scheduled more efficiently from home.
Biggest teaching moment ▶ 27:47 Framework for founder operational involvementJesse educates Alex on when a founder must directly run a channel to eliminate translation layers using the example of Carolyn running Facebook ads for Unbloat.
Alex holds their own ▶ 43:15 Citing mega-event financials and marginsAlex demonstrates deep domain expertise by citing the revenue, operating models, and 30-50% profit margins of industry behemoths like Informa and Ascential.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Alex as informed peer | Guest teaching | Guest disagreement | Alex pushing back | Why |
|---|---|---|---|---|---|---|
| Welcome to The Crazy Ones and Listener Shoutouts | 3 | 2 | 1 | 1 | A friendly check-in and mindset conversation about dealing with sickness, internal guilt, and building sustainable habits. Both hosts share personal reflections with zero friction or hostility. | |
| Early-Stage Company Values and the Ownership Mindset | 5 | 4 | 2 | 2 | Alex and Jesse explore company culture and employee ownership mindsets. Alex contributes his Morning Brew framework of pull versus push employees, while Jesse challenges the common trope that equity is necessary to instill an owner mentality. | |
| Mastering Candor, Difficult Confrontations, and Management Standards | 4 | 5 | 2 | 2 | Jesse shares insights from running executive staff meetings and maintaining radical candor without judgment. Alex openly admits his personal difficulty with confrontation and fear of being disliked, allowing Jesse to share best practices from Apple and Red Ventures. | |
| Founder Therapy: The Costs of Scrappiness and the Startup Rollercoaster | 4 | 5 | 2 | 2 | Alex conducts a founder therapy session regarding his hands-on scrappiness with The Plunge. Jesse playfully calls Alex out for self-criticism and explains frameworks for when a founder should master a channel versus delegate it. | |
| Reflections on SXSW and Measuring Conference Return on Investment | 5 | 4 | 3 | 4 | Alex questions the true ROI of conferences following his SXSW trip and pushes Jesse on whether conference meetings could just as easily be arranged virtually. Jesse pushes back by highlighting the sheer velocity and impact of in-person interactions. | |
| Analyzing Conference Business Models and Event Startup Playbooks | 7 | 4 | 1 | 2 | Alex demonstrates strong industry knowledge by detailing the financial models, margins, and acquisition multiples of conference giants like Informa and Ascential. Jesse complements this with unit economic breakdowns and niche event launch strategies. | |
| Startup AMA: When to Double Down vs. Shut Down a Venture | 6 | 5 | 2 | 2 | Both hosts answer a listener AMA regarding when to shut down versus double down on a business. Jesse outlines timeboxing and upside ceilings, while Alex provides clear milestone criteria for his venture The Plunge. | |
| Episode Conclusion and Listener Call to Action | 2 | 0 | 0 | 0 | Standard wrap-up segment with a call to action for listener emails and YouTube subscriptions. |
Statements from this episode (16)
Pujji: Growth Assistant employs 25 internal staff and 300 offshore contractors
“Our internal staff there is about 25, then we have like 300 GAs working for clients”
Pujji: Startups should define core values at five to seven employees
“Even when a company is five, six, seven people, I think that's kind of the right time to start the values conversation, because It sort of gives people a guideline. It's leverage for the founders to kind of give them a guidepost for what people will do when th…”
Pujji: A company's real values are defined by compensation and promotion decisions
“Every company has values, whether stated or unstated or whether lived or unlived, right? It's whatever people get paid, promoted, hired, fired based on, like, it's how those decisions are made.”
Lieberman: Early-stage startups require proactive pull employees over order takers
“In the early days of the brew, we'd always, I always thought of it as like, there's two types of employees. There's pull employees and there's push employees. Pull employees are the people that pull the entire business forward. Push employees are the people yo…”
Pujji: Claiming employees must have equity to act like owners is manipulative
“I don't think you have to own part of the company. And I think that's like a faux narrative oftentimes that founder, you know, founders will somewhat be manipulative around, oh, everyone's an owner here.”
Pujji: Apple requires leaders to know operational details three levels down
“Apple requires that you know the details of your organization three levels down. So if you're a VP and the reason they do that is just a very, like, this is part of just why it's important to be super buttoned up or know the answers or know, know your numbers …”
Lieberman: Scrappiness can trap founders into harmful frugality
“First of all, like, I think scrappiness can lead to frugality, and frugality truly, like, isn't necessarily a good thing.”
Lieberman: Morning Brew founders lacked skills to allocate millions in cash flow
“It was the fact that we were bootstrap founders, and as we were starting to cash flow millions of dollars in the business, we didn't have the skill of how to allocate all of that money because we had never dealt with that much money in our lives.”
Lieberman: The Hustle Began as an Events Business in San Francisco
“The hustle started as an events business, and, like, it started as a single tech event for Early stage founders in San Francisco.”
Lieberman: SXSW generated $325M economic impact for Austin in 2017
“It came out that at in 2017, South by Southwest drove three hundred and twenty five million dollars in economic impact to Austin. One hundred and sixty five million of that was All around attendance was ticket holders, credentials, et cetera. And then you add …”
Lieberman: Informa's events business generated $395M revenue in 2022
“Informa is a twelve billion dollar UK based business. Just their events business did three hundred ninety five million dollars top line. In 2022.”
Lieberman: Events businesses can achieve 30% to 50% profit margins
“Events businesses can be 30 to 50% margin businesses like they're super profitable.”
Lieberman: Ascential generated $375M in 2017 from events like Cannes Lions
“There's another one called Essential. This is the business that owns CanLion and Money. 20 20. They did three hundred and seventy five million dollars in 2017.”
Lieberman: Ascential acquired Money20/20 for $100M when it generated $40M annually
“That, that conference, at least pre-pandemic, was doing forty million dollars a year, and it was acquired by Essential, the business that owns CanLion, for a hundred million bucks.”
Pujji: New founders should give a startup a two-year timebox
“If you're a new, new founder starting out, I typically say like, give yourself two years. If you don't have anything going interesting within two years, Then probably you should do something else. Two years is a long time if you're giving it your all every day…”