In the startup world, we have people we like to call “serial entrepreneurs.”

A serial entrepreneur is basically a startup founder who has ridden the entrepreneurial merry-go-round more than once.

That’s because founding a startup that makes it to a big exit is an extremely profitable (though grueling) endeavor. A really skilled founder can make hundreds of millions of dollars or more, doing just that.

That’s why, when I see a truly talented entrepreneur, I’ll often jump on the deal – even if I don’t quite “get” their business plan.

Take serial entrepreneur Jack Dorsey, for example. When he first started his business – a mobile credit card processing platform called Square – some investors weren’t so sure about the idea.

But they backed him anyway. Why? Because Dorsey is the man behind Twitter, one of the most successful tech companies of all time.

Trusting in the founder’s expertise turned out to be the right move. Today, Square is worth more than $30 billion.

Of course, even the greats come up with bad ideas sometimes. That’s why I run every single pitch through my 7-question gauntlet, which you can find here.

But a skilled founder knows the intricacies of steering a startup towards success, and that counts for a lot.

In addition to “street cred,” serial entrepreneurs have a Rolodex full of past investors, advisors, venture capitalists and board members.

And, since they all made money the last time they backed this founding team, they’re more likely than not to sign on again.

That’s because, in startup-land, it’s just part of the unspoken law: if an entrepreneur you backed rewards you with a big return, it’s good form to support them in their future endeavors.

On the other hand, if you’ve never invested in a startup before…

Backing an entrepreneur with a history of big exits is a pretty reliable way to succeed.

Until next time,

Neil Patel


Comments

34 responses to “Your Angel Investing Philosophy: Back the Jockey, Not the Horse”

  1. Does Neil have a list of startups that he can send out to us that he is investing in, or future startups that he himself is putting money in?

  2. you will get nothing but philosophy and for me that is all so far don’t know ware to start. Received a call from Kirin but missed it the call back No. does not work 866 310 1498

  3. Have read everything sent to me and am really ready to proceed, but have not figured out exactly where to start….still waiting for something in the mail that I can have with me all the time,

  4. I felt the same way, so I just would look at all the investment startup recommendation, then go with that, read all about them an click invest, then you set up an account with wefunded. First Then invest.

  5. Good afternoon, I was under the impression I was supposed to receive a kit a well. Haven’t received anything. I have invested in 4/5 startups thus far

  6. I’m new to all of this also. I did receive a nice welcome package with goodies in it & a book that I need to start reading. I’ve already completed my profile, linked up a bank account and I’ve jumped in to two investments and am on a wait list for a third. So all is going well so far. I’m pleased.

    • That’s great” you can only start where you are comfortable. There is a lot a lot reading and comprehension. With that”
      I have not invested as of yet but my profile is completely done the information I retrieve from Republic was my guide to viewing future investing and I will. You can’t participate in every single portal the same day. But the information is here to move forward in my o.

  7. cann’t seem to know where to start i paid 499 and still haven been told how and when to buy. does the money for the start up go for the payment to invest. charlotte hileman to much information to try and figure out where to start need some help.

    • Hi Charlotte,

      Sorry for the confusion! If you’re a member of the Angels & Entrepreneurs Network, you can find all your deals at angelsandentrepreneurs.com. This website, The Startup Investor, is a free educational newsletter that you get as a bonus to your subscription.

      Hope this helps!
      Neil

  8. Hi Neil
    I’m knew and I have never done this before, but I have heard of this and that’s why I joined. But a lot of the terms I don’t know what they mean. For example what does seed mean? What risk are involved. I apologize if that’s seems like a dumb question, but I know absolutely nothing. But I’m very excited

    • Hi Monica,

      I completely understand. Silicon Valley lingo is tough to learn at first! I’d suggest reading the dictionary we put together, which you can find by clicking here. I hope this helps!

      Neil

  9. That’s great” you can only start where you are comfortable. There is a lot a lot reading and comprehension. With that”
    I have not invested as of yet but my profile is completely done the information I retrieve from Republic was my guide to viewing future investing and I will. You can’t participate in every single portal the same day. But the information is here to move forward in my opinion.

  10. Hi. I’m Regina Williams and am also new to investing, although it’s something I’ve always wanted to do. I found it helped to review the videos and Republic has a step by step guide on how to invest, what to look for in each company and the importance of reviewing all info that’s given about the company to help make an informed decision. Also I found Neil’s deep dive very help. I haven’t invested yet but I think after all my reading and looking at all videoa in media center I’m ready to do my 1st deal. Thank you Neil for making Angel Investing possible for the little fish like. I’m so excited and determined to swim like a Shark.

  11. Hi I am new and my first invested is in the monogram orthopaedice wondering how long it usually takes to see a return I am thanking three to four years

  12. This is my 4th time doing good his. I keep getting a error. I am tired of all the hype , discussions , or whatever you want to call it. I joined this venture (1st time) to get results. The only thing I’m hearing is what if you had invested in Amazon, Netflix etc…
    I want to know the names of companies that I can invest in. Time is running down , I’m ready to invest.

  13. I don’t quite understand. How do you know when your investment pays off. Where is the proof that you gave them money. How would you tale your money out if you really needed to? How do they pay you dividends?

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