The Warren Buffett of the Internet Returns | Andrew Wilkinson on My First Million

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Key Takeaways

  • The truth is that real innovation is stressful; it involves a ton of failure and leads to an unhappy life:
    • “I’d way rather own 10 car dealerships and sit on them for 50 years, live a nice life, have lots of kids live somewhere I like, hang out with my friends than spend 50 years trying to innovate and do something crazy and launch rockets to Mars, but have a miserable life.”Andrew Wilkinson 
  • Success has a price:
    • “There’s a lot of personal sacrifice here. They’re 45 and they don’t have kids. They’re super stressed, they’re sick all the time, they don’t sleep, etc.” – Andrew Wilkinson
  • The world is filled with innovators:
    • “The world is super competitive and if Steve Jobs hadn’t done the iPhone, a year later someone else would’ve” – Andrew Wilkinson
  • 3 ways to a meaningful life, choose one: 
    • 1) Do whatever it takes to make yourself happy
    • 2) Make the biggest impact or contribution to society possible
    • 3) Win and challenge yourself to achieve as much as possible
  • If you want to scale a business, just hire someone who’s done it before:
    • “The advice I always give people is if you want to build a business that is going to scale and do well, just find someone who has already done it before” – Andrew Wilkinson
  • Angel investing isn’t as sexy and profitable as most people think:
    • “I have a $10 million venture portfolio and if I had just taken that same money and put it in the S&P 500 or Apple stock or anything else, I would be way richer. And it would be way safer. I’d have a more liquid net worth.”Andrew Wilkinson 

Intro

Books Mentioned

Enjoying Life vs. Making It Better

  • Andrew recites a quote from EB White: “I wake every morning trying to decide if I want to enjoy the day or make it better” 
    • Andrew would rather enjoy his day than try to make it better
  • The truth is that real innovation is stressful; it involves a ton of failure and it leads to an unhappy life:
    • “I’d way rather own 10 car dealerships and sit on them for 50 years, live a nice life, have lots of kids live somewhere I like, hang out with my friends than spend 50 years trying to innovate and do something crazy and launch rockets to Mars, but have a miserable life.”Andrew Wilkinson 
  • When Andrew read about Steve Jobs, he learned that although Jobs was a genius, he was also an asshole and wasn’t very unhappy
  • Success has a price:
    • “There’s a lot of personal sacrifice here. They’re 45 and they don’t have kids. They’re super stressed, they’re sick all the time, they don’t sleep, etcetera.” – Andrew Wilkinson
  • The world is filled with innovators:
    • “The world is super competitive and if Steve Jobs hadn’t done the iPhone, a year later someone else would’ve” – Andrew Wilkinson
  • 3 ways to a meaningful life, choose one: 
    • 1) Do whatever it takes to make yourself happy
    • 2) Make the biggest impact or contribution to society possible
    • 3) Win and challenge yourself to achieve as much as possible

Starting A News Outlet

  • Andrew and his company owes about 30 companies and has invested in about 80 companies
  • Andrew recently started a local news outlet, Capital Daily, a newsletter that covers the city of Victoria
    • It has 40k subscribers in a city of 200k. Capital Daily is now bigger than the local newspaper.
    • He’s invested a couple of hundred grand and recently hired journalists to create original articles
    • He monetizes through affiliate ads, where returns can be higher than regular ads. Although he admits it’s not the world’s best business, he envisions replicating the model in different cities with each newsletter generating $200k-$500k in profits.
  • The newspaper business has gone from one of the best businesses to be into one of the worst in only a few decades. The question is if you apply modern technology and a new business model, could you make it extremely profitable again?

Advice From Andrew

  • The people you work with can make a great job crappy or a crappy job great:
    • “It doesn’t really matter what the settings are if the people are awesome” – Andrew Wilkinson
  • If you want to scale a business, hire someone who’s done it before:
    • “The advice I always give people is if you want to build a business that is going to scale and do well, just find someone who has already done it before” – Andrew Wilkinson
      • E.g: McDonald’s used its expertise to help Chipotle scale their business 
  • You want your business to be fundamentally strong so even if you hire a subpar CEO, it won’t be affected much:
    • “I think the key is buying businesses where they can withstand a mediocre CEO where they’re already organically growing so well and their business model is so simple that it’s hard for somebody to fuck it up” Andrew Wilkinson
  • The person who makes the decision should be responsible for the action. If you’re the CEO and you need to make layoffs, don’t blame the board because you’ll vilify them and employees will resent them.
    • “Every tough decision has to be the CEO” – Andrew Wilkinson
  • Angel investing isn’t as sexy and profitable as most people think:
    • “I have a $10 million venture portfolio and if I had just taken that same money and put it in the S&P 500 or Apple stock or anything else, I would be way richer. And it would be way safer. I’d have a more liquid net worth.”Andrew Wilkinson
      • “I don’t think that angel investing is a good way to make money. I think it’s a good way if you’ve got a good network in San Francisco and you invest in your friends, you’ll probably do okay. There are easier ways to make money.” 

Million Dollar Challenges

  • Andrew would try to create the 2.0 version of the Million Dollar Homepage
  • There are many apps that generate millions in profit with little overhead:
    • Donald Trump/celebrity voice imitators
    • Plant identifiers
  • Sam would create a lead generation business for irrigation, trucking, or home renovation
  • Hunt for products on Product Hunt: A lot of great developers aren’t marketers so their idea, although good, fizzled out or didn’t catch the attention it needed to be successful
    • You can probably buy their product for cheap and then try to turn it into a huge business

Additional Notes

  • Hello Landing is a network of fully furnished apartments in cities all across the country that you can rent out and live in
    • It’s cozier to live in a furnished apartment than a hotel so it appeals to business travelers
  • Sam invested in the seed round of glucose monitoring startup Levels. Shaan and Andrew didn’t invest because Levels doesn’t own its own hardware, but are very bullish on the market overall.
  • Andrew is creating Mailman (in beta), a Gmail plugin that will have many of the same features as Hey. Mailman will deliver emails only a few times a day and blocks first-time email addresses.
My First Million : , , , ,
Notes By Alex Wiec

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