Real Leaders

An Angel Investor’s Guide for New Entrepreneurs

An entrepreneur, first and foremost, is an idea person. They think differently, create opportunities where resources didn’t exist and are willing to take significant risks to pursue a thought to action.

Surprisingly, I have found that an advanced business education degree can get in the way of entrepreneurship. I’ve met people who’ve earned an MBA, that describe how their college classes led them to overanalyze everything and talk themselves out of all of their good ideas. 

In order to be an effective entrepreneur, you need to take risks and get real-world experiences. This requires going beyond any classroom curriculum. Can you imagine any analysis predicting that Starbucks would open a store on every corner, sell coffee for three times the price people were used to paying and, in addition, capture the lion’s share of an existing market, while growing by many multiples? I certainly can’t. 

As I began to navigate the entrepreneurial world, I learned a few tips along the way. Below are a few that I found helpful for anyone interested in becoming an effective entrepreneur: 

Be Optimistic

Starting a business will not be easy. There will be hurdles in fundraising, challenges to hiring, and frustrations around messaging and understanding the marketplace. Throughout the hard times, you must remain optimistic. 

As a founder, you set the tone for the business. Your excitement and general happiness will be infectious to your team. 

Look at problems not as roadblocks, but rather as puzzles that can be solved. In difficult moments, you should be open to learning from others and explore meaningful experiences. Different perspectives will also allow you to see problems in different ways. 

Be Realistic

Optimism and realism need to co-exist. While some ideas are great, not all stand the test of time, will adapt to changes in society or threats from competitors. 

DVDs dominated the at-home entertainment industry in the early 2000s until the streaming options of Netflix, Hulu and Amazon disrupted how we consume movies and television. I also think few people will argue that having music playlists stored on mobile phones has become obsolete today. 

The reality is – you need to know when to stop. 

Recognizing this is just as important as recognizing opportunities.

If you have proven that your idea is dead, just let it go. Sometimes, you need to cut your losses and move on in order to preserve your most valuable asset — your time. 

Often entrepreneurs fail because they make the mistake (sometimes repeatedly) of becoming fixated on pursuing whatever they believe is a good idea without truly analyzing if that idea can make money. 

If your business fails because you didn’t move fast enough and your competition did a better job of building an effective sales force, then address that issue in your next business. In my opinion, failure can be a great teacher if you ask yourself, “Why did I fail?”

If you answer that question, you can prevent yourself from failing again.

Look for a Mentor

Entrepreneurs can find mentors through networking or personal connections. A good start would be to attend industry meetups, local talks and conferences. You must be present to find the right people. 

Even if you cannot connect directly with an entrepreneur you admire, there are still ways to learn from them.

I like Richard Branson. I learn from him from a distance by following his blog, reading his books and reading news about him. He’s a mentor to me, despite the fact I don’t have a personal relationship with him. 

Accelerators and incubators can also be tremendously helpful as you start your first business. To be accepted into an accelerator program, you must first apply in a selective application process. If you’re selected, you will typically be given a small investment and access to a large mentorship network comprised of venture capitalists, startup executives, and experts in the industry. Accelerator programs usually have a set time frame to allow companies to work with these mentors; to plan out their business and avoid potential problems in the future. 

In contrast to accelerators, startup incubators begin with entrepreneurs or companies that are earlier in the process of starting their business and may not operate on a set time frame. Generally, incubator programs require startups to relocate to a specific area to work with other companies in the incubator. Once they are there, a company will receive help with refining their ideas, creating their business plans, working on product-market fit, networking, etc. 

It’s important to find a mentor (or mentors) who will challenge you to go outside of your comfort zone and give you reliable advice. The best type of mentors are those that will tell you the truth, even if you don’t want to hear it, because that’s the only way you can truly grow. Change doesn’t happen when you’re comfortable and if you want to be an effective entrepreneur, you can’t be afraid of that.

Find a Co-Founder You Trust

There is an African proverb that says, “If you want to go fast, go alone; if you want to go far, go with others.” 

Not only can the right co-founder make your life easier, but they will also make your business more fundable, considering venture capitalists prefer to fund companies with two to three founders as opposed to just one.

You need to be proactive when choosing your co-founders, preferably individuals who have different strengths than you. I started my first company, Autoweb, with my brother. He had the software engineering skills to build the product and I had the vision on how to sell it. Our skills were complementary and together we grew a business to a $1.2 billion market cap. 

While diverse backgrounds and skills in your business leadership can make a better impact with developing ideas and strategy, you want to limit the total number of founders to no more than four. Too many founders will reduce your ownership, and potentially make it difficult to build consensus during the early days of the business as you all try to agree on a strategic path and make numerous decisions on a daily basis. 

Create a Service-Oriented Culture

Don’t let greed drive your ambition. Author Simon Sinek writes in The Infinite Game, that businesses and individuals become the best version of themselves when they are inspired by a higher calling — one that embraces service to the community and environment. 

Giving, whether in time or financial support, needs to come from the heart. Get your company involved in service from day one, and nurture a culture that considers social impact. 

Genuine service efforts will infuse your business with a soul and bring you and your team true joy and fulfillment. Above all, it’s necessary to take care of your people. Nothing will be more valuable when it comes to building a successful business than having a reliable team who will stay with you for years to come.

Don’t Compare Yourself to Others

Don’t compare yourself to the handful of entrepreneurs who have become celebrities and whose Tweets make headlines. For every one of these media darling entrepreneurs, there are thousands of quietly struggling entrepreneurs. The road to success is a deeply personal and unique journey. At the same time, success looks different to different people. Stay true to who you are as an individual and as an entrepreneur and set goals that work for your business. 


No good story is without conflict. There is little doubt that you’ll eventually run into obstacles both big and small — no matter what stage of business you’re at. You need to prepare yourself to work hard and get excited, to be able to overcome setbacks and roadblocks. Don’t ever allow problems to sideline your motivation. Success against the odds is always satisfying. 

Business is about relationships — not just with customers and your team, but with yourself. All relationships take commitment and time, but the good ones should ultimately prove to be worth pursuing. 

Enjoy the journey

Too often people are impatient. There are entrepreneurs who tirelessly work towards the day they IPO, have huge profits, or an exit. Enjoy the journey. Life is primarily made up of our journeys and not milestones. Our journeys have to be meaningful.  

I always tell my wife that our vacation starts the moment we leave the house and head to the airport. You should enjoy the journey as much as the destination.

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