Sep 6, 2021 • Podcast

How do I sell to entrepreneurs?

Paul wraps up his decision-maker series with some tips on selling to entrepreneurs.

Show Notes: 

Entrepreneurs may take more risk because they answer to no one but themselves. This means you can take some risk in your presentation.

It’s critical that you understand their vision. How will your solution help them achieve that vision?

Don’t waste their time. Provide a detailed agenda.

Entrepreneurs are willing to go against the grain. Appeal to their contrarian nature.


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How do I sell to entrepreneurs?

(Transcribed from podcast)

Here’s the question: How do I sell to entrepreneurs? I don’t know if you guys remember this, but about a month and a half ago, I did this whole series on different types of decision makers. We talked about financial CFO-type executives; we talked about selling to procurement buyers, selling to technical-type people. And I told you, “Hey, on our next episode, we’re going to talk about selling to entrepreneurs.” Guess what I forgot to do. I forgot to record that episode on how to sell to entrepreneurs. So that’s what we’re going to talk about on today’s show.

Before we get into that, though, a quick shout-out to Andrea over at The Creative Impostor Studios. Podcasting, you know, it continues to grow in popularity. And, in fact, the timing right now is perfect to launch your own podcast. Or if you were looking to make a change and you’d need help with your current podcast, reach out to Andrea and her team over at The Creative Impostor Studios. They are here to help you. They do a great job. And I can’t say enough nice things about Andrea and her team. So, if you do want to connect with them though, we’re going to have a link over to her website on this episode’s webpage. So please check it out.

Also, I’ve been talking about Selling Through Tough Times, that new book I have coming out. It’s delayed just a little bit because of supply-chain constraints and COVID stuff going on, so the book’s going to be delayed by about a week or so. So it’s going to launch in early October. But until then, I would encourage you to visit our website,, and you can learn more about the 30-Day Tough-Timer Challenge. I was just talking to a buddy this morning about the Tough-Timer Challenge and how it can help you build mental resilience and help you reshape your attitude. It’s an absolutely wonderful tool. And the best part is, it’s absolutely free. There’s no charge to download the documents that you need. Check it out at our website, We’re going to have all the details you’ll need on the website. So, we’ll have the link to that on this episode’s webpage as well.

So, let’s get back to that question: How do I sell to the entrepreneur? You know, I’m going to share a couple of thoughts, some examples from what I hear from salespeople. But we created that archetype of the entrepreneur and what’s it like to sell to them. And I want to talk about what’s important to them, how you should craft your message.

So, when we think about this, what does an entrepreneurial business owner care about? What is important to them? Well, their business, right? Obviously, their business is an extension of themselves. They’ve created it; they’ve built it, and they’re constantly thinking about it. They’re constantly thinking about it. So, they’re deeply passionate about their businesses. They’re fully committed. And what’s interesting about how they make decisions is that they’re willing to take on a little more risk than maybe a corporate type of decision maker. And here’s why I say that. The entrepreneur typically answers to no one but themselves. They have the ability to make a decision that may be unpopular, that may be full of risk, because they are the ones they answer to if that makes sense. They have to look in the mirror and deal with the consequences. So, what I’ve found, in my personal life as well, in selling to entrepreneurs—and other salespeople told me the same thing—it’s okay to be a little risky in your presentation. You can take risks.

Let your entrepreneurial spirit show when you are presenting to these types of decision makers. They’re going to appreciate it. It will resonate with them. So let your entrepreneurial spirit show when you are presenting to them. That’s a hard word to say, by the way, entrepreneurial. There we go. Got it.

Next thing, understand their vision. It’s critical to understand where they are going, where they want their company to be. Understanding their vision is really you understanding the entrepreneur themselves, because they are an extension of the company, as I mentioned earlier. So, figure out where they want to be three to five years from now. In fact, that would be a great question. When you’re sitting down with an entrepreneur, just ask them, “Hey, your vision for your company? Where do you see your company three to five years from now?” This is a great question as well, because it stretches their time horizon. It gets them thinking long term, where they focus on the outcomes they want to achieve.

Once you identify where they want to be three to five years from now, you must demonstrate exactly how your solution will help them achieve that vision. How will your solution help them be where they want to be three to five years from now? And, if nothing else, your solution may help eliminate roadblocks that they could potentially experience on the way to achieve that vision. I’ll give you an example. I do a lot of work in the insurance industry, and one thing I’m toying with right now is that a broker who is selling an insurance policy to an entrepreneur—a business owner. Let’s say that business owner says, “You know what? Three to five years from now, I want to have two more locations; I want to double the size of the business; I want to continue to grow. I want to expand new products, do all this.” The insurance provider, the broker who is partnering with that entrepreneur by providing their solution, which is insurance, they’re basically eliminating some of the risk—things that would get in the way of them achieving that vision or goal. Whether it be a natural disaster, whether it would be, you know, a fire, whether it be a lawsuit, cyber attack, whatever it may be, they can help eliminate some of that risk, which, in turn, is going to help them achieve their vision, or at least not prevent them from achieving their vision. But to do all this, you’ve got to understand their vision.

Now, another piece here, when you are selling to entrepreneurs—do not waste their time. They are very time sensitive. Time is their most valuable commodity because they can always make more money, but you can’t always make more time. So, it’s important, when you are presenting to them, you have a detailed agenda of exactly what you are going to cover—what’s important to them, but also, when you’re presenting your solution, you don’t want to overburden them or create an additional burden for them to have to overcome. You have to be able to demonstrate how your solution is easily integrated. It’s pain-free. It’s not going to create any additional work for them. Now, they will delegate some of this work, and that’s fine. But we have to emphasize how your solution is not going to cost them their time. Their time is absolutely critical.

Now, going hand in hand with the understanding vision piece, we also need to demonstrate how our solution will accelerate what they are trying to build. You know, most entrepreneurs I know, and most of the salespeople I trained who work with entrepreneurs or sell to them or work for one, they’re impatient. Meaning, they’re not good at just sitting back and waiting for things to happen. They’re going to do what they can to accelerate their growth, accelerate to their vision. So, as the salesperson, it’s critical for you to demonstrate how your solution will help them achieve their goals much quicker.

For example, we asked the entrepreneur, “Where do you see your company five years from now?” And they say, “Well, we want to have double the locations. We want to grow by this amount.” And you could then say to them, “Well, what if partnering with us we could help you achieve that five-year vision in three years?” Think about how powerful that is. How could you help them achieve their vision sooner than they expected? And the goal here is to demonstrate how your solution will accelerate the timeline to achieve so that you can shorten that time frame.

Last thing before we call it an episode. If other organizations, other mainstream companies, dismiss your solution, tell the entrepreneur. They are contrarians by nature. They’re willing to go against the grain. And if you meet with an entrepreneur and then tell them, “You know, I’ve tried to sell this solution to several different organizations, and they just say they’re not open to it. Imagine what they’re missing out on.” And what you’re doing here is you’re tapping into that contrarian spirit of the entrepreneur. They’re willing to go against the grain. In fact, if many of their competitors refuse the solution that you’re providing, that might create an even greater opportunity for you. They see it as a way to gain ground. So really, they’re contrarians by nature. So they’re not as concerned about the social proof of, “Hey, this is a well-established solution.” If you’ve got something new that’s innovative, they’re going to be all about it. And if other people are dismissing it, they might even be more in tune with it, more open to it, and more willing to try it out.

And here’s what I mean. I’ve got one group of salespeople I’m working with. It’s a newer company. They had a new, innovative product in the software industry. And with this company, what they notice is, when they would go and talk to entrepreneurs and they would say, “Look this is brand new. It’s revolutionary, and everyone else has dismissed it. All the mainstream companies, the market leaders in your industry are putting it aside. They’re saying the product is too new and that it’s not necessarily needed. But what they don’t know is that this product is going to revolutionize the industry. You could be one of the first to use it, to integrate it.” When they would go to an entrepreneur and pitch it that way, they noticed the buyer immediately was interested in the solution. And part of it was just because of the newness, the prestige of it, the fact that other people were dismissing it.

All right, folks. Well, just a quick recap here on selling to entrepreneurs, a couple of tips. Number one: you can take risks in your presentation. Let your entrepreneurial spirit show. Understand their vision. Understand their vision and then demonstrate how your solution will help them achieve their vision and, in some cases, even accelerate the timeline to achieve that vision. Make sure you’re not wasting their time. Time is their most precious commodity. And then, finally, it’s okay—it’s okay if other mainstream companies dismiss your solution. [To the] contrarian entrepreneur, that might make it more appealing.

Make it a big day.

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