Paul English on entrepreneurship, startups, and tech

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.comfinancial 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
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Notes By Stan Rizzo

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