When it comes to startup investment, there are a few names that stand out from the rest. These individuals have had a tremendous amount of success in helping startup businesses get off the ground, and they offer valuable lessons for anyone looking to invest in a startup. If you’re looking for startup investment, it’s important to learn from the successes and failures of those who have come before you. In this blog post, we’ll take a look at some of the most successful startup investors of all time and see what we can learn from them. In this blog post, we will discuss some of the most successful startup investors of all time and what you can learn from them.
Andy Bechtolsheim

One of the most successful angel investors in history, Andy Bechtolsheim has made a name for himself with his $100k investment into Google in which he exited for just over 1 billion dollars (now that’s a return on investment) and now his estimated worth is around 11 billion dollars! His startup investment career actually began a few years earlier. Bechtolsheim co founded a startup called Sun Microsystems, which was later acquired by Oracle. Andy had a rocky start, but the experience taught Andy an important lesson about investing in startups: don’t be afraid to invest in a company that isn’t doing well. In fact, he believes that it’s oftentimes the companies that are struggling the most have the most potential as they are trying to solve the biggest challenges.
Lesson: Don’t be afraid to invest in a startup that isn’t doing well – they may have more potential than you think. Just make sure they have a good team with a revolutionary product or service!
Naval Ravikant

Naval Ravikant is the founder of AngelList, a startup that connects startups with investors. He has been involved in over 100 startup investments and is known for being extremely selective when it comes to choosing which startups to invest in. Naval’s philosophy on startup investment is heavily based on opportunity cost – he doesn’t want to miss out on the next big thing, so he’s willing to invest in a startup even if it has a low chance of success.
One of Navals most successful start up investments was in a company called Uber, which is now worth an estimated $62.0 billion.
Naval has invested in over 121 companies in a wide variety of sectors with 38 successful exits. This is a staggering number, but it’s important to remember that startup investment is a high risk/high reward game.
Lesson: Don’t be afraid to invest in a startup with a low chance of success – you may just hit the jackpot! But remember to diversify.
Tim Draper

Tim Draper is a startup investor who has had success with investments in companies such as Tesla, Skype, and Baidu. He is also the founder of Draper Fisher Jurvetson (DFJ), one of the most successful venture capital firms in the world. DFJ has made over 300 investments in early stage companies and has a portfolio that includes some of the most successful startups in history, such as SpaceX, Hotmail, and SolarCity.
Tim investment style can be best described as aggressive. He’s not afraid to invest a lot of money in a startup with the hopes that it will become the next big thing. This strategy has paid off for him, as many of his investments have turned into huge successes.
His investments in bitcoin and blockchain technology make him a vocal advocate, not just for himself but also on behalf of other entrepreneurs who might be interested in this new emerging market.
Lesson: When it comes to startup investment, experience is key. If you want to be successful, invest in a company that has a team with a lot of experience in the industry.
Mark Cuban

This notorious Shark Tank star is a startup investor with a portfolio that includes companies such as Dropbox, Uber, and Airbnb. He is also the owner of the Dallas Mavericks and one of the wealthiest people in America.
Mark Cuban’s investment style can be summed up in two words: high risk/high reward. He is not afraid to invest in a startup that has a high chance of failure as long as the potential upside is high. This strategy has paid off for him, as many of his investments have turned into huge successes.
Cuban’s most successful startup investment was in a company called Broadcast.com, which was the first online streaming company. This shows Mark isn’t scared to be ahead of the curve when it comes to startup investment.
Lesson: Don’t be afraid to invest in a startup that is ahead of its time – But do your research first.
What Can You Learn From These Investors
Take risks but don’t go all-in
All of these investors have one thing in common: they aren’t afraid to take risks when it comes to startup investment. However, they’re also not reckless with their money. They only invest in a startup if the potential upside is high enough. Do not put your entire net worth into a startup.
Do your research
Before investing in a startup, make sure you do your homework. Know everything you can about the company and the team behind it. Research isn’t just limited to the startup itself, you should also look into the industry it’s operating in.
Diversify
No one knows which startup will be a success, so it’s important to spread your risk by investing in several different companies. This will increase your chances of hitting the jackpot.
Experience is key
As mentioned earlier, experience is key when it comes to Startup investment is a high risk/high reward game. The best way to minimize your risk is to invest in a company that has a team with a lot of experience in the industry. The team should not only have experience but so should you, by having a deep understanding of the sector you are investing in you drastically increase your chance of success.
Final Thoughts
So, what can you learn from the most successful startup investors of all time? First and foremost, it’s important to have a clear vision for the future of the business as most startups fail within the first three years and you should be able to articulate the business in a way that grabs people’s attention. You also need to be passionate about the product or service and have the drive to see the business through thick and thin. And finally, don’t be afraid to take calculated risks – as long as they are calculated risks. If you can embody these qualities, you too may become one of the most successful startup investors out there.
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