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Great conversations run long. Their best ideas don't have to.
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Shaan's Question: The Idea Maze Behind Hampton
Shaan praises Hampton's name, brand and idea, and asks Sam about the paths he considered and rejected. Sam explains he did his research publicly, with guests who ran similar companies.
- •Shaan asks about the rejected names, target markets and runner-up ideas behind the polished result
- •Sam deliberately did his research in front of people
- •Sam told the guests before and after that he was thinking of launching something similar
- •Shaan frames the process as wandering the idea maze
Failed Ideas: Short-Term Rentals and Truckers
After selling The Hustle, Sam spent months exploring ideas. He rejected a short-term rental business because he didn't enjoy it, and a trucker audience because he liked the idea more than the work.
- •Sam bought an Airbnb that did okay, but he found it a pain and outside his zone of genius
- •He built the STR Crew Facebook group, which drew people who shared their blueprints
- •Sam grew up in a trucking family and considered building a YouTube audience of truckers
- •He liked the idea of blue-collar workers more than being around them, and compared it to a neck tattoo
What Hampton Is and the Wrong Audiences Tried First
Sam describes Hampton as a peer group with small groups, a digital community and events. He then lists the audiences that didn't work: marketing executives, doctors, Fortune 500 CEOs and minorities, before settling on CEOs.
- •Hampton has an eight-person group, a digital community and around 200 events a year
- •It is inspired by Chief, YPO and Vistage
- •Sam ran 50 to 70 meetings with marketing executives and none wanted it at about $10K a year
- •Doctors, Fortune 500 CEOs and minorities were dropped for lack of access or founder fit
- •Founder fit made CEOs a no-brainer, and he did research by interviewing members of other groups
Naming the Company: Streets of St. Louis
Sam explains that he names his companies after streets in his St. Louis neighborhood. He shares the runner-up names and how he settled on Hampton.
- •Sam didn't know what The Hamptons were until he was about 27
- •Runner-up names were Macklin, Sublette, Simpson and Kingshighway
- •Hampton comes from Hampton Avenue near where he grew up, and he says it doesn't mean The Hamptons
- •He asks only a few people, such as his wife and business partner, for a gut opinion
- •Marriott owns hampton.com
Hiring a $15K Branding Agency
Sam explains the branding agency he hired for $15,000 and the brief he gave it. The brief was built around 'Elite, but cheeky' and old ads from brands like Rolex and Porsche.
- •The one-line brief was 'Elite, but cheeky', inspired by Felix Dennis
- •Sam collected 1970s ads from GQ, Porsche and Rolex
- •He chose British Racing Green, his favorite color
- •He wrote sample sentences he wanted on the website
- •He calls hiring a branding agency a total hack
Things Sam Said No To: Curation and Delegating Interviews
Shaan asks what Sam said no to along the way. Sam says he and his partner Joe watch every interview and approve or deny every applicant, turning down revenue to keep the group focused on CEOs.
- •Hampton gets roughly 100 applicants a day and accepts a fraction
- •Sam and Joe watch 100% of interviews and are the only ones who approve or deny
- •Chief let in everyone and grew to $100 million in revenue, and Sam says turning people away hurts
- •He thinks about Kingsford Charcoal and what could be made from rejected applicants
- •They stay focused on CEOs of one type of business
Shaan's Advice: Show the Curation and Lean on the Founder Story
Shaan suggests Hampton should advertise how selective it is, for example with a counter of revenue turned away. He also says Sam should use the founding story, and Sam agrees he erred by trying to keep it from being about himself.
- •Shaan says the heavy curation would make him want to join, so it should be shown on the website
- •Sam says a founder can be the face for a while and phase out later
- •Shaan says the founder doesn't deliver the service, so the founder as face isn't a problem
- •The origin is the San Francisco peer group that led to the podcast and to The Hustle
- •Sam says Shaan was right that he couldn't build a huge company that way, but he didn't need to
- •Shaan says Sam was aiming for a company that makes him millions rather than a billion-dollar one
Shaan's Experience With Branding Agencies
Sam asks whether Shaan has used a branding agency. Shaan describes working with a single designer on The Milk Road and rewarding the team with a brand at a subscriber milestone.
- •Shaan used one designer, Jeremy, for The Milk Road, and Sam thinks it turned out well
- •The mood-boarding process felt indulgent for a business with no revenue
- •They planned the brand reward for 100,000 subscribers
- •Shaan sees a brand as a luxury, but a necessity for something like e-commerce
Shaan's $25K Naming Agency Mistake
Shaan describes paying a naming agency $25,000 and calls it a rookie mistake. He found the people interesting and picked up a useful process, but the name was forgettable and the app had already failed.
- •Shaan says the better move would have been to hire the most interesting person from the agency in-house
- •Three people came in and pressed him to explain the essence of the company
- •He kept a slam-poetry-like process for getting to the essence, which he finds useful as a copywriter
- •Flashcard personality-quiz exercises annoyed him, and he can't remember the name
- •The app had already failed by the time they delivered the name
Recap and Takeaways
Shaan recaps the episode: research in public, repeated false starts before finding the customer, the street-based naming, the branding brief, and using a founder story. Sam says he got $25,000 worth of free advice.
- •Five false starts on who the customer is, each tested by contacting people, ended with the obvious idea
- •Shaan says the name is awesome but isn't sure the street-naming approach is easy to copy
- •He suggests showing the brief Sam gave the branding agency, on the idea of garbage in, garbage out
- •Shaan says a founder story is very powerful
- •Sam says he needs to fix the founder story gap
Publisher timestamps
- 0:00Intro - A radically transparent look inside Hampton launch.
- 2:32Idea #1: Short-term rental crew (failed)
- 3:32Idea #2: Community of truckers (failed)
- 4:23Idea #3: Community for entrepreneurs
- 5:48Fail #3: V1, V2, V3 of Hampton
- 8:00Step 1: Research
- 10:08Step 2: Picking the right name
- 12:05Step 3: Hire a Branding Agency ($15K)
- 14:12Things Sam said no to
- 17:12Leverage the founder story
- 20:18Shaan's branding agency experience
- 21:51Shaan’s $25K Mistake: Hiring a "naming" agency
- 25:57Takeaways
