What to Look for in an Entrepreneur
Last week I was catching up with an entrepreneur who was thinking about doing some angel investing, and he asked me what I look for in other entrepreneurs. Over the years, I’ve had the opportunity to

Last week I was catching up with an entrepreneur who was thinking about doing some angel investing, and he asked me what I look for in other entrepreneurs. Over the years, I’ve had the opportunity to work with many great people and learn from their experiences. Entrepreneurship is not a one-size-fits-all journey, but I’ve found some common characteristics that show up again and again in successful entrepreneurs.
1. A Desire to Improve
There are constant ups and downs in entrepreneurship. One moment you’re high-fiving your co-founder after signing a new customer, and the next a key employee leaves and you just want to curl up and cry. The entrepreneurs who succeed have a deep desire to improve. They want to learn, grow, figure out what works and what doesn’t, and take lessons from others who have gone before them. This thirst for learning is a key trait.
2. A Unique View on Risk
Many people see starting a new venture as too risky. Entrepreneurs, on the other hand, often have enthusiasm for calculated risk, especially risks that look uncertain or unlikely to succeed to the average person. They either have a unique angle or an unusually strong belief that they can overcome the challenges. This different perspective on what is and isn’t risky is a defining characteristic.
3. A Chip on the Shoulder
Almost every entrepreneur I’ve worked with has had some compelling drive or unusual background that pushes them to prove themselves in an extreme way. The old saying holds true: chips on shoulders equal chips in pockets. In other words, entrepreneurs with something to prove often end up creating significant value for themselves and their investors.
4. MacGyver-Level Resourcefulness
Resourcefulness is another common trait. The best entrepreneurs love to “MacGyver” their way into opportunities, finagling introductions, connecting seemingly unrelated dots, and figuring out how to make progress when others would stop. Whether it’s landing a first customer, solving a daunting problem, or raising a round of funding after many rejections, this tenacity and creativity greatly increase their chances of success.
5. A Glass-Half-Full Outlook
Finally, successful entrepreneurs tend to believe they can change the world, an industry, or even a city. This optimism, sometimes born from blissful ignorance, helps sustain them when progress is slow, opportunities are scarce, or things are going wrong. A positive outlook creates space for unexpected magic, where unexplainable good outcomes seem to come together at just the right time.
These five characteristics—desire to improve, unique view on risk, chip on the shoulder, resourcefulness, and optimism—are some of my favorites when it comes to entrepreneurial success. There’s no guaranteed formula and no single path, but these traits consistently show up in entrepreneurs who make it.
If you’re thinking of becoming an entrepreneur, or considering partnering with or investing in one, keep these characteristics in mind. Evaluate them against the entrepreneurs you’ve met in the past. You’ll likely see these traits reflected in those who have succeeded.