How to Pitch an Entrepreneur
There are a seemingly endless number of articles written on how entrepreneurs can improve their pitch to investors. However, in practice the pitch meeting is very much a two-way street. Entrepreneurs pitch VCs, but VCs also pitch entrepreneurs.
Founders of promising companies often have no shortage of options for capital. From the first interaction, the entrepreneur is trying to figure out if the VC is the right partner for the business. In turn, the best VCs are focused on how they can pitch entrepreneurs on the value they bring to the table.
Based on hundreds of pitch meetings I have been a part of both as an entrepreneur and investor, I’ve outlined how I’ve seen the best VCs approach the pitch meeting, leaving a great impression and increasing the likelihood of securing a deal:
1. Do your homework — It is the VCs job to build a prepared mind ahead of the meeting, allowing entrepreneurs to go deeper on the business faster.
I remember pitching one VC during a partner meeting a few of years ago: two minutes and one slide into the meeting the VC said “We understand the market, product, and opportunity. Let’s flip to the roadmap and unit economics.” This was not only impressive but I appreciated the directness in not wanting to waste time. We covered a lot of ground that meeting. Another VC told me they had already spoken with 2 of our publishing partners and had very specific questions around our plans to expand our partner pipeline. I was impressed by the hustle. Yet another VC sent a company I work with a reverse pitch deck — a pitch deck on the market opportunity that they saw — ahead of the first meeting.
On the flip side, one well-known VC asked me how I was going to compete with a large incumbent in a completely different market. I later learned he confused us with another startup with a similar name. Not so impressive.
2. Make the pitch meeting a two-way conversation — As an investor, the pitch meeting is an opportunity to show the entrepreneur what working with you will be like. But many investors stumble out of the gates by not making the meeting a two-way conversation.
Instead, they watch the entrepreneur flip through the slide deck for an hour with little interruption, saving most questions for the end. When the questions do come it feels more like a press conference than a conversation, with little follow-up or feedback after the questions are answered. The entrepreneur will read this lack of engagement as lack of interest, and they also won’t learn very much about the style, approach, or personality of the investor.
On the other hand, the best pitch meetings let the back-and-forth between investor and entrepreneur be the center of gravity, with the slides just used for support. The VC is both asking questions and providing insight, and the founder is doing the same. This feels more like a collaboration in which both sides are working together, as opposed to one where the entrepreneur is constantly convincing the VC.
When done right, this approach is a valuable and positive experience for the entrepreneur. The most enjoyable pitch meeting I had at my last company was in a very large board room with more than 10 people from the fund, myself, and my co-founders. Several times my co-founder Andrew and one of the VCs were essentially shouting at one another in a very heated, but well-spirited debate. The level of engagement left us with an incredibly positive impression. And we learned quite a bit during that meeting as well.
3. Focus on the product — Founders spend most of their day thinking about their product and customers. VCs spend more of their time thinking about broader markets and deals. This can lead each side to steer focus to diverging aspects of the business during the pitch meeting. VCs that actively have used the product, focus on customer response, and have smart questions about the product roadmap show founders they are differentiated. They also demonstrate that they are not overlooking the most important part of building a business — making a product that a large number of people want.
4. Get tactical — Entrepreneurs by nature enjoy being tactical about operating a business— otherwise they wouldn’t have started, much less survived, the early years of company building. How do I hire faster? How do I close our dream sales prospect? Should I hire a VP Finance or a CFO? Do I need a brand marketer or a direct response marketer? In contrast, many investors spend more time on macro questions: Where is the VR market going? What technologies will create the next big breakthroughs? Where are we in the market cycle?
There is obviously nuance here and crossover, but in general entrepreneurs tend to spend more time on, and value, tactical thinking. More than likely the entrepreneur is dealing with many tactical problems on the day of the pitch meeting. As an investor, if you can elevate those and provide actionable feedback that is helpful, you can quickly create memorable differentiation.
5. Go on the journey with the entrepreneur — Creating a business from nothing requires figuring out ways to make seemingly impossible things happen, and doing so repeatedly. Great investors may do the same, but the nature of the VC job is that most investment decisions are a “no.” As a result, investors sometimes gravitate to all the reasons why a business won’t work, as opposed to why it will.
Despite this, I’ve found the best investors are willing to be optimists and go on the journey with the founder during the pitch meeting. This is not to say they don’t have concerns or questions — rather that they are open-minded and start from a place of belief. These VCs want to hear the optimist’s take and truly take it in. If after the meeting the pessimists take sets in, so be it. But going on the journey as opposed to being closed-minded during the pitch meeting will leave the entrepreneurs with a positive impression.
Final note — As a VC, the pitch meeting is an opportunity to give the entrepreneur a glimpse into what working with you will be like. Just as the entrepreneur must refine their pitch, the investor must refine theirs. Further, it is likely that this approach will help with the actual investment evaluation as well. At minimum it will ensure founders leave the pitch meeting feeling that their time was well spent, and excited to work with you in the future, on their current company or the next.
