An Entrepreneur’s Guide to Making a Great First Impression


First impressions are almost instinctual. I meet with several hundreds of startups every year and within the first ten minutes of a meeting, I begin to gather critical information about the person sitting across from me in an effort to sense whether they have what it takes to be a successful entrepreneur. 

I’m often asked what are the key signs I look for in an entrepreneur. Below are seven signals I have noticed that make a lasting impression when evaluating an entrepreneur.

1. PASSION. How passionate are they about their idea? Through posture, demeanor and words you can immediately tell if they have a burning and committed passion to their startup, which is essential. Do they have that fire in their eyes when they speak about their customers pain points and explain the unique way their teams will solve this? Passionate entrepreneurs have an urgency and strong resolve to solve the challenge at hand and they know exactly how they want to go about it.

2. TEAM DYNAMIC. Since businesses are not built by a single person, I try to meet with the entire founding team. I can often sense the team dynamic from the minute they enter and even better once we start talking about the issues, solutions and vision.  I look for chemistry between the founders. Are they clear on who is the CEO? Are they on the same page in terms of vision? Do their skill sets compliment each other? I enjoy seeing teams that seamlessly build on one another’s ideas, yet each has their specific area of expertise that they bring to the team. In early conversation it is obvious when each team member knows exactly when it’s their turn to chime in, and the nods of approval follow.

3. CONTEXT. A good entrepreneur has a clear vision why they are doing what they are doing. I look for whether they spent the time to understand the real market context – need, size, approach – of their target customers. It’s not about waking up one morning and getting excited about an idea. I get worried when I seem to know more about a market than the entrepreneur sitting across from me. Knowing the context of the business you are going into is key to tackling the challenge at hand.

4. LEANING IN. Not all entrepreneurs are necessarily charismatic extroverts — and that’s ok. However, in order to turn a technology into a business they need to be pro-active about presenting their thoughts. Even body language they display can give me a great sense if they are pro-active about their startup. It’s beyond the passion, it’s about explaining, assuring, and convincing me that they are on the right track and prepared to ride the waves. I have had experiences on both sides of the spectrum. Those that have come to sit back and reflect and those who came to engage, sell and lead the discussion.

5. RESILIENCE. As an entrepreneur, you will hear the word “no” on a daily basis.  People will try to tell you that there isn’t a real problem or your solution exists already. This is why it is critical for an entrepreneur to be resilient. How do they approach the downturns that come up along the way? What are they doing to not get stuck in the mud and bogged down from the details? More than once (a week) I’ll run into an entrepreneur that has been working 24/7 on their business and can be convinced in minutes that their endeavours are moot. That’s not going to get them very far.

6. LISTENING & LEARNING. I meet with lots of extremely smart entrepreneurs that know much more than me on many subject matters; however two skills that makes some stand out more than others are listening and open mindedness. I look for a balance of confidence and an open mind. Great entrepreneurs, no matter how intelligent or well versed in their subject area, are constantly seeking out information, trying to learn more about their market and really listening to feedback in order to pro-actively improve on what they are striving to accomplish.

7. DO THEY HAVE THEIR SH*T TOGETHER? Finally, everything runs smoother when entrepreneurs “have their sh*t together.” Are they prepared for the meeting? Do they have an objective to drive meaningful conversation? Have they explored other possibilities for getting what they are looking for – help, connections, investment? Preparation for the meeting not only makes it much more effective, but also demonstrates respect which is a highly valued trait for your future clients, employees and investors.

It is amazing how much critical insight can be gleaned about an entrepreneur and their team from the first few minutes of a conversation. Most of the companies I meet with have a mix of the traits mentioned above, but only a few really hone them. At UpWest, we are continuously looking for the diamonds in the rough, the entrepreneurs that have and will do everything it takes to create a really big and meaningful business. These are the folks we are looking for and enjoy creating lasting relations with. 

— Gil