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Do you have what it takes to make it as a startup founder? Do you have what investors are looking for in an entrepreneur that should get funded?

Having worked with countless entrepreneurs and interviewing some of the most active angel investors on the DealMakers Podcast in today’s startup ecosystem, it’s clear that there are some consistent patterns in what it takes to survive and thrive within the entrepreneurial journey, and take a venture from idea to a meaningful business.

If you’re not sure if you’ve got the right stuff, or you’d like to get a head start in making smart angel investments yourself - here are some of the things top investors have filtered out in the founders that ultimately perform the best.

Will Herman

Will Herman has sold two of his own ventures for over $700M, and has invested in 82 startups. If you want a shot at getting funded by Will, here are the four things he looks for in founders.

1) Founders who are interested in building a great team around them. That’s not only cofounders but that’s ultimately the total management team that’s in the company. Founders who know what they don’t know are really valuable.

2) Founders that focus on execution more than their idea. Will says, “I just don’t believe that there are that many unique ideas and that the uniqueness of your idea really isn’t that important.” A good team can execute on a mediocre idea and make it great, and make a great company. It’s all about execution.

3) Founders who constantly talk to their real and prospective customers. So many startups are building products, creating services that are meeting needs in their heads, not actual needs. It’s ultimately lack of product market fit that kills most startups, not lack of funding. So, understanding what your customers need, want and think is critical.

4) Old school hard work. Will says, “The person who works more hours is almost always going to succeed or do better than the person who works fewer hours. I just believe in it. I believe those who are dedicated to what they’re doing and are willing to work to achieve it have a fundamental advantage.”

Fabrice Grinda

Having made 400 plus startup investments and achieving at least 150 exits make Fabrice Grinda as one of the most experienced investors alive.

In our exclusive DealMakers interview Fabrice says it’s all about amazing storytellers. Because when you’re an amazing storyteller, and you have great control of your numbers and your vision, you’re going to be able to raise money at every stage.

You’re going to be able to hire better people. You’re going to be able to talk to the press. That means capital favorably leans towards extroverts versus introverts. Storytellers who are smart and greedy, and at the top of their numbers. Or in a better position to raise than others. In fact, Fabrice says, “ if you have a greedy storyteller, you kind of hit the homerun in terms of what you want to have.”

Michael Litt

Michael Litt has been named top 30 under 30 and entrepreneur of the year. He now heads up seed stage funding firm Garage Capital.

If you want to get funded by Michael’s group he says, “You know what we really look for is really, really, really talented product and technical leadership with domain expertise.

So, if you’re building product for a specific market or an ecosystem, ideally you have experience in that world to have real user and product empathy. Then on the other side of the business, we look for what we call a chip on the shoulder or the warrior instinct.”

Adeo Ressi

Adeo sold two companies for $1 billion before he was 30 years old. As founder of the Founder Institute, Adeo is looking for talented, motivated individuals who are working on those ‘zero to one’ startups and are willing to commit to several months of intensive focus and are accountable for making things happen.

Thomas Korte

Thomas is cofounder of Angel Pad, whose companies have raised over $1.4 billion, in addition to the $80 million the accelerator has raised itself.

The traits he sees shared among the most successful founders include:

  • Investing the time to learn about the fundraising process
  • Having that immigrant spirit of being willing to move and go for it
  • Those who are opinionated, but are willing to adapt according to the data
  • Ability to keep making decisions and moving forward

Kevin O’Connor

Kevin is the founder of Double Click and initial investor in another unicorn that sold to IBM for over $1 billion.

If there are three things Kevin looks at in founders they are:

  1. A sense of urgency. It’s not putting it off until tomorrow
  2. The ability to be skeptical, especially about technology, and really focusing on what problem they are solving
  3. Being willing to break the rules. Willingness to look at the status quo and to do something that’s a little bit perceived to be a little bit crazy


We hear a lot of rumors about what investors are looking for in founding teams, and what can increase the odds of getting funded.

There is a lot you can do as an entrepreneur to better position yourself for success and capital. Yet, it is also interesting to see how each fund and angel investor can really hone in on different traits and qualities they have seen deliver success from their experience.

So, often winning the fundraising game is equally about getting in front of the investors who are the right match, and who are looking for what you’ve got.

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Most of us connect to the internet through our ISPs (Internet Service Providers). When you do that, your data travels through a network of routers to reach its destination.


Usually, it’s completely unencrypted (i.e. plain text). Even if it has some encryption, some information remains visible – like your IP. It’s needed to communicate with the internet with no issues.


On top of that, your ISP can easily see what you’re up to online… and worse, so can anyone who monitors your connection. This includes the websites you browse and the files you download.

How does a VPN make your connection private?

When using a VPN, a secure “tunnel” is created between the provider and the end-user (that’s you!). VPNs operate on the same lines everyone else uses on the internet. There is an important distinction: the data is scrambled to create a private connection.


Your information travels back and forth privately via this encrypted “tunnel”. Using this encrypted “tunnel,” information travels back and forth between the user and the VPN provider. If somebody tried to decrypt it, they would have to have an access key. Without it, that’s essentially impossible!

What is the “tunnel” in Virtual Tunneling Protocol?

The virtual tunnel referred to in the acronym VPN isn’t actually a tunnel at all. A physical tunnel between two locations would involve a direct link between them.


WAN access was used in a similar way before VPN technology spread throughout the world. So, virtual tunnelling uses a method called encapsulation to literally wrap your data in a layer of secure encryption. This is the “virtual tunnel” we are creating when we use a VPN.

Why would I want to use a VPN?


The era we live in is one of connectivity. While it has many advantages, it unfortunately also has a lot of risks. There’s a growing number of cyber-threats and generally a lot of unsolicited attention in our lives.


Not all of it is malicious. For example, advertisers may want to collect your private information for marketing reasons. But they do compromise your privacy, and that’s something many people value – and a lot more should.


If you want to be more private online, or don’t want anyone to spy on you, using a VPN is an easy – and simple – choice to make.


VPNs also provide other nifty benefits. For example, you can access content that’s not available in your country. You can also protect yourself on public WiFi, and even get better prices when you shop for airline tickets! There are quite a few more use cases, and you can find all of them here.

Is it legal for me to use a VPN?

This will vary depending on your country or region.


Many countries have no laws banning or restricting the use of VPNs. For example, the United States, Canada, and the United Kingdom don’t restrict the use of VPNs. Neither do countries that belong to the European Union.


North Korea, China, Russia, and Iraq, on the other hand, restrict or outright ban the use of VPNs.


You’ll want to check your local laws for an up-to-date answer to this question.

Are VPNs easy to use and configure?

Consumer VPNs are very easy to set up! Most VPN services, including Surfshark, have easy-to-use apps that handle the majority of the setup for you. If you can open a web browser or log in to your email, you can use a VPN.


VPN services do include complex security and privacy features. Luckily, the applications take care of them on their own! You’ll probably only need to enter your login information, select the server you want to connect to, and that’s it!


The server you select will provide websites and servers you connect to with a proxy IP. That way, nobody will ever know where you’re truly connecting from.


VPNs used to require some technical know-how to establish and secure, but that’s no longer true. If you were intimidated by the VPN setup process in the past, you shouldn’t hesitate to dive in right now!

VPN Protocols and Security


So, how can a VPN protect your data? It uses security encryption on all packets that are transmitted to and from your computer to the provider. Specific details – including how effective it is – vary from protocol to protocol.


Generally, encryption works by scrambling the information that is transmitted. Anyone attempting to view it without the decryption key will be looking at gibberish.


Decryption keys are shared in different ways, too. It depends on the encryption protocol itself and how its configured. Here’s an easy way to think of these keys: picture an impenetrable locked file cabinet. It’s safe, but you need one of your coworkers to access it.


So, what do you do? Simple – you give them a key. Now, they can open this cabinet and access the files whenever they need to. Of course, in reality, actual encryption key sharing is more complicated. Some methods are more “secure” than others, but it’s a realistic way to picture how key encryption works.


There are a few common VPN protocols currently in use:


  • PPTP
  • L2TP/IPSec
  • OpenVPN
  • IKEv2
  • SSTP


Here’s a quick glimpse at two popular secure protocols and how they work:


OpenVPN is one of the most reliable open source software choices. It’s trusted and recommended by the leading internet security providers, such as Surfshark. OpenVPN guarantees fast performance and top-notch encryption.


Paired with robust encryption algorithms, OpenVPN supports data transmission protocols UDP and TCP.


OpenVPN is used for Surfshark’s Windows app and manual router configurations.


‘Open source’ also means it is continuously improved and developed by the security community worldwide.


IKEv2 (also known as Internet Key Exchange Protocol Version 2) is the most recent and advanced protocol. It’s way faster than most protocols and is really good at maintaining a stable VPN connection.


This tunneling protocol was developed by Microsoft and Cisco. Currently, it’s considered the most reliable in terms of performance and security

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Main Network Protocols

There are three main network protocols for use with VPN tunnels. These protocols are generally incompatible with each other. They include the following:


A set of protocols developed by the IETF to support secure exchange of packets at the IP layer. IPsec has been deployed widely to implement VPNs. IPsec supports two encryption modes: transport and tunnel.


The Point-to-Point Tunneling Protocol is a technology for creating VPNs, developed jointly by Microsoft, U.S. Robotics and several remote access vendor companies, known collectively as the PPTP Forum.


Layer Two (2) Tunneling Protocol is an extension to the PPP protocol that enables ISPs to operate Virtual Private Networks (VPNs).

Consumer Versus Corporate Services

Consumers use a private VPN service, also known as a VPN tunnel, to protect their online activity and identity. By using an anonymous VPN service, a user's Internet traffic and data remain encrypted, which prevents eavesdroppers from sniffing Internet activity. VPN services are especially useful when accessing public Wi-Fi hotspots because the public wireless services might not be secure. In addition to public Wi-Fi security, a private VPN service also provides consumers with uncensored Internet access and can help prevent data theft and unblock websites.

Companies and organizations will typically use a VPN to communicate confidentially over a public network and to send voice, video or data. It is also an excellent option for remote workers and organizations with global offices and partners to share data in a private manner.

Virtual private dial-up network (VPDN) Explained

One of the most common types of VPNs used by businesses is called a virtual private dial-up network (VPDN). A VPDN is a user-to-LAN connection, where remote users need to connect to the company LAN. Another type of VPN is commonly called a site-to-site VPN. Here the company would invest in dedicated hardware to connect multiple sites to their LAN though a public network, usually the Internet.

Looking for Free VPN Services?

Free VPN usually refers to services and tools that let you browse the Web securely and anonymously. The tools are typically available for desktop and mobile Web browsing. Read Webopedia's 5 Free VPN Services article to learn more.