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Obama’s rumored speaking fee sparks a deep dive into the economics of speeches
Sam asks Shaan to guess what Barack Obama charges for a speaking engagement, and the numbers quickly escalate into seven figures. This sets up the episode’s core theme: paid speaking as a surprisingly lucrative business.
- •Sam asks Shaan to estimate Obama’s speaking fee
- •Shaan guesses a mid–six-figure range and acknowledges it could be higher
- •Sam shares he’s heard rumors of a $1M–$1.2M range
- •They react to the idea that top figures won’t speak for less than seven figures
Sam’s awkward street encounter: mistaking a stranger for Hasan Minhaj
Sam tells a story about chasing down someone he thought was the comedian Hasan Minhaj, only to realize he had the wrong person. The interaction turns from intensely embarrassing to oddly redeeming when the stranger recognizes Sam from the podcast.
- •Sam spots someone in New York City he believes is Hasan Minhaj and runs after him
- •The person denies being on any podcast, causing Sam to panic and feel embarrassed
- •Sam worries the interaction could be interpreted as stereotyping
- •The stranger then reveals he actually listens to My First Million, easing the tension
Cringe-moment nightmares and social mishaps they can’t forget
Shaan and Sam riff on the kinds of micro-embarrassments that haunt them, describing them as the stuff of nightmares. Shaan shares a particularly painful holiday-party mistake that still sticks with him years later.
- •Shaan describes nightmares centered on accidentally misnaming someone for a long time
- •Sam adds examples of saying the wrong automatic response in conversation
- •Shaan shares a story about asking a woman about her pregnancy when she had already had the baby
- •They discuss how these moments linger emotionally long after they happen
Bragging rights: the show’s chart performance and why it might be happening
The conversation shifts to the podcast’s rankings, including being number one in entrepreneurship and business for a period. They discuss what rankings mean, why the show might be climbing, and what promotions and guest sharing can do.
- •Sam says the show hit number one in business and entrepreneurship during the week
- •Shaan notes charts reflect momentum and a “secret formula,” not absolute size
- •They attribute growth to strong episodes and guests promoting (including email lists and heavy sharing)
- •They talk about the surreal feeling of being listed near well-known shows and personalities
Listener culture and catchphrases: “no small boy stuff” and “Dillon the dog”
They highlight how listener memes and phrases have become part of the show’s identity. A tweet praising the show becomes a potential new motto, and Sam shares fan encounters in New York.
- •Shaan reads a tweet calling it the best entrepreneurship podcast: “Big money… No small boy stuff”
- •They riff on adopting “no small boy stuff” as a motto
- •Sam recounts listeners approaching him in New York
- •Fans reference “Dillon the dog,” a recurring bit from a past episode
What speakers get paid: Shaan’s fees, Sam’s take, and celebrity benchmarks
Sam asks about Shaan’s paid speaking, and Shaan describes how strange it feels to be paid significant money to talk. Sam argues Shaan is undercharging and shares real-world price points from events, including HustleCon and other bookings.
- •Shaan says he usually turns down paid speaking but has done it and finds the numbers surreal
- •Shaan gives an example of quoting $10K and being quickly accepted
- •Sam says that rate is undercharging
- •Sam shares what he paid Casey Neistat (fee plus a one-way private flight) and what Gary Vaynerchuk asked for
- •Sam mentions his own speaking pay range and what he heard about Ashton Kutcher’s fee
How books, “bestseller” labels, and speaking gigs reinforce each other
Shaan explains a playbook he heard from a would-be author: books can be a tool to unlock better-paid speaking opportunities. He contrasts earnest “professionally curious” creators with more skeptical interpretations of motivational-speaker culture.
- •Shaan recounts meeting someone who said the real reason to write a book is to get speaking gigs
- •He describes using chart positioning to claim “bestseller” status and raise speaking rates
- •Shaan frames the earnest version as people trying to be “professionally curious” about a topic
- •He contrasts that with a more cynical view of scammy guru-style motivation content
- •Shaan shares how he once imagined a podcast as a more flexible route than constant travel
Negotiating leverage and perks: Sam’s travel-only approach and De Niro’s contract demands
Sam explains he sometimes prioritizes first-class flights and a week-long hotel stay rather than direct speaker fees, turning speaking into a personal travel opportunity. He then shares a detailed list of perks Robert De Niro required for a film, using it as an example of extreme negotiation.
- •Sam describes saying yes to speaking only if the trip is appealing and fully covered for him and his wife
- •He shares details from a Wall Street Journal item about Robert De Niro’s deal terms for a short shoot
- •The asks include private jet travel, accommodations, and additional vacation time
- •They react to the negotiation style as resembling a hostage negotiation
Speaker bureaus and transparent fee lists: exploring wsb.com and the middleman model
Shaan introduces wsb.com as a place to browse notable speakers and get a sense of booking fees. They discuss how speaker bureaus act as aggregators and middlemen, and why the model is an interesting niche business.
- •Shaan connects the topic to Coach K and how speaking/endorsements can rival a salary
- •He mentions the site listing speakers and approximate fee tiers (example: Coach K at “70,000+”)
- •They describe the business model: agencies that match event demand with a roster of speakers
- •They treat speaker booking as a niche worth examining as a standalone business
From YouTuber management to “Twitter boys”: a new kind of speaker agency idea
Sam compares the evolution of YouTuber celebrity to today’s internet creators and asks when “Twitter boys” and podcasters will get the same agency treatment. Shaan argues the demand already exists and points to examples like Cameo moving upstream into corporate appearances.
- •Sam recalls how internet creators were once dismissed as not “real” celebrities
- •He references a management company that manages MrBeast and how large that business can become
- •Sam suggests a similar agency could represent podcasters and Twitter personalities
- •Shaan says creators already get paid to speak, but haven’t been “rolled up” into bureaus
- •Shaan cites Cameo as evidence people pay for access and notes its push toward higher-end appearances
How big is the speaker-bureau business? Washington Speakers Bureau revenue surprise
Sam shares acquisition and revenue figures for Washington Speakers Bureau to illustrate the scale of the industry. Shaan reacts and adds a social tip about guessing low when someone asks you to estimate a number.
- •Sam asks Shaan to guess Washington Speakers Bureau’s revenue
- •Sam says it was doing $15M around the time it was acquired in 1999/2000
- •Sam says it reached $150M in revenue by 2017
- •Shaan shares a “homie move” rule: guess low so the reveal can be surprising upward
Paying for guests and who would be worth $100K: fame vs conversation quality
They discuss rumored pricing for booking big names and debate whether spending $100,000 for a podcast guest would be worth it. The conversation weighs click potential against having a great, natural conversation with someone who fits their style.
- •Sam mentions hearing a rumor about booking Arnold Schwarzenegger for $100K
- •They question whether a guest would deliver $100K worth of value through promotion or impact
- •Shaan asks who they’d choose if they had a $100K guaranteed-guest budget
- •Sam prioritizes ultra-famous figures for volume, but says Elon might be uncomfortable to interview
- •They discuss the appeal of guests who rarely do content and would “show up and give a shit”
Update on EggCartons.com: Sarah Moore’s acquisition story and extreme hustle tactics
Shaan returns with a detailed update after emailing Sarah Moore a Google Doc of questions, and she replies with a remarkable story. She describes building a search process with unpaid interns, buying the business with debt and a seller note, and doing outrageous outreach to get owners to respond—plus wild anecdotes from sourcing and travel.
- •Shaan explains he sent Sarah Moore a short question doc and she replied after initially suspecting spam
- •She says she started a solo, nontraditional PE-style search with no fund and used over 50 unpaid interns from Craigslist
- •She claims they sifted through hundreds of thousands of private companies over a long search before finding EggCartons.com
- •She describes aiming for 100% ownership via debt financing, with the business cash flow as collateral rather than personal collateral
- •She recounts contacting many banks, getting rejected, and closing with bank debt plus a seller note, with professional fees rolled into the deal
- •She shares unusual personal and operational anecdotes (research studies, aggressive outreach, fake IDs for library access, international sourcing incidents)
- •She reframes the company as specialty packaging and says a significant portion of the business is unrelated to eggs
