December 11, 2022
Paul English: How He Built And Sold 6 Companies And Why He Believes Irritation Becomes Inspiration | My First Million with Shaan Puri & Sam Parr #394
Check out the Episode Page & Show Notes
Key Takeaways
- Paul English has sold six companies, most notably Kayak for $2B, and is currently working on his seventh company
- Paul’s internal rate of return is around 30.5% over the last several years across 60 investments
- He has some “famous misses”, which include Airbnb, YouTube, Snapchat, and Dropbox
- “Team first, customer second, profit third.” – Paul English
- Magical teams create magical products, and magical products tend to create profits
- After successfully recruiting a talented person, Paul asks them, “Do you know anyone more amazing than you?”
- Companies fail because of a founder implosion or because it is trying to solve a problem that no one cares about
- “It makes me sad when I see a beautiful product that solves a problem I don’t care about.” – Paul English
- Find something that irritates you in your daily life and create a product that resolves that irritation
- Paul questions whether a person like Elon (the richest person in the world) should have as much power as he does (control over the world’s richest source of information)
- Paul thinks Elon will do something interesting with Twitter, but he’s more interested in all the Twitter replacements that will come out
Intro
- Paul English (@englishpaulm) is an entrepreneur and Kayak co-founder. He has founded 7+ companies and is currently investing at Boston Ventures Studio. You can find his work and interests at PaulEnglish.com.
- In this conversation, Paul, Shaan, and Sam discuss business ideas, Paul’s famous missed investments, how to be an elite recruiter, and why he wants to create a competitor to Twitter
- Check out these Podcast Notes from MFM’s conversation with Dharmesh Shah
- Host – Shaan Puri (@ShaanVP) and Sam Parr (@theSamParr)
Paul English’s Background & Previous Companies
- Paul has sold six companies and is now working on his seventh
- His largest sale was Kayak for $2 billion in 2013
- His previous companies:
- Boston Light (a Shopify-like e-commerce company)
- Intermute (internet security software)
- GetHuman.com (customer service)
- Kayak (travel and booking)
- Moonbeam (podcast player app)
- Lola (business travel and expense)
- Paul blew through his 401k to finance one of his companies, which he eventually sold for $30M
Paul’s Famous Misses: Airbnb, YouTube, Snapchat
- Paul met Brian Chesky at Airbnb when the company was financing at a billion-dollar valuation
- Paul “missed the bigger picture” with Airbnb, and didn’t think that enough people would want to live in strangers’ homes
- When working on Kayak in Sequoia offices, Paul was introduced to Chad Hurley and Steve Chen, the co-founders of YouTube
- Paul didn’t quite get the videos online thing either
- “I have some famous misses.” – Paul English
- Paul’s internal rate of return (IRR) is around 30.5% over the last several years across 60 investments
- He also missed Snapchat when it was financed at an $80 million valuation
- He met the founders of Dropbox early on and didn’t invest
- Paul still shares some concerns about Dropbox’s security model
Paul English’s Big Hits
- Pilot.com – financial services software for startups and growing businesses
- Paul got to know the founding team of Pilot.com prior to their creation of it and chose to invest in the team for whatever project they decided to launch next
- He invested in Pilot.com at a $30M valuation and now the company is worth 40x at $1.2B
- Kensho – a competitor to a Bloomberg terminal
- Paul knew Kensho’s CTO because he used to work at Kayak
- Kensho was a 22x for Paul (not bad)
How To Become An Excellent Recruiter
- “Team first, customer second, profit third.” – Paul English
- It is optimal for the founder to become a phenomenal recruiter
- Minimize stress in the office
- Magical teams create magical products, and magical products tend to create profits
- Always, always be recruiting and trying to connect with people
- After successfully recruiting a talented person, Paul asks them, “Do you know anyone more amazing than you?”
- The first five people you hire will hire the next 50, and those 50 will hire the next 500
Deets: Paul’s Next Billion-Dollar Idea
- Paul started Deets in 2022 in an effort to fix the online review process
- He believes this social media app meant for socializing could become a billion-dollar business
- Deets provides recommendations from your friends, influencers that you choose to follow, and people that are similar to you to help you find the best restaurant, hotel, etc.
- Yelp is a 20-year-old dinosaur that behaves like the mafia: restaurant owners have to pay Yelp to clean up the bad Yelp reviews on their restaurant
Is Starting A Company Easier After Selling Multiple Companies?
- Some people lose their edge after selling a company because they’ve achieved financial sovereignty, which may decrease performance
- Others use the capital they’ve generated to reduce frictions in their subsequent pursuits, which may increase performance
- Companies fail because of a founder implosion or because it is trying to solve a problem that no one cares about
- “It makes me sad when I see a beautiful product that solves a problem I don’t care about.” – Paul English
- Paul owns about 300 domain names and is obsessed with branding and good names
Irritation Becomes Inspiration
- Find something that irritates you in your daily life and create a product that resolves that irritation
Ideas Paul English Is Working On
- Paul built middle.net to make it easier to meet “somewhere in the middle” when the group is all in different locations
- Paul created funcontact.com to make contact sharing (at conferences, for example) easier
- As someone diagnosed with bipolar disorder, Paul created bipolarsocialclub.org to further destigmatize bipolar disorder
- “TSA is a joke. The stuff they do to you gives you a false sense of security, but there’s no real security with TSA.” – Paul English
- Someone should create something that improves TSA
Elon Musk and Twitter
- “Put me on the list of a thousand people that want to create a Twitter competitor right now.” – Paul English on Elon Musk’s takeover of Twitter
- Paul sees the Elon takeover as a bit of a “sh*t show”
- He has forgiven Elon for some of the stupid stuff he’s done because Elon has created such good products
- The way that Elon fired people at Twitter was “obnoxious as f*ck”, according to Paul
- “You’re the richest guy in the world. Do you really need also to be an a**hole? There was no reason you had to march people out of the office.” – Paul English
- Paul questions whether a person like Elon (the wealthiest person in the world) should have as much power as he does (control over the world’s richest source of information)
- The eight-dollar verification thing is a joke
- Paul thinks Elon will do something interesting with Twitter, but he’s more interested in all the Twitter replacements that will come out
- Paul wants to create Kind Twitter, Inc. where there are no trolls, cruelty, or misinformation without filtering out the independent information
