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Selling to People You Know (Episode 6)

Harris talks about the deals that can be the fastest to close—and the most frustrating—when you are selling to people you know. We also talk about Transistor, the podcast hosting service, and the latest improvement in Intro CRM that can track deals by billable hours or units sold.

⚠️ Please note: This is an old episode of the Pipeline Meeting podcast. In August 2022, the show relaunched in a new format. For the most recent episodes, please visit the podcast page

Show Notes

In this episode, Harris talks about how selling to people you know can jumpstart your business. It can also be a source of frustration as those deals may never close. Whether it’s friends and family or past colleagues, these are people you know and who you in return. So, should you avoid selling to people you know? Harris shares two tips that can make this source of sales worthwhile.

This episode also kicks off a series focusing on tools that you can use to grow your business like Transistor, an independent and bootstrapped company that makes a tool you can use to start your own podcast. Transistor is a great company, they make a beautiful product, and they make it easy for you to publish and distribute your podcast. Learn how to start a podcast.

Lastly, we touch on the latest features in Intro CRM. These features are built for freelancers, solopreneurs, and early stage founders who may not necessarily think of their deals in terms of revenue. Maybe you don’t know what deals are worth, or are focusing on your sales in a different way to hit traction. Maybe your prices are locked in and it’s really the number of clients that matters. In any case, Intro CRM makes it easy to track your deals.

Show Description

Pipeline Meeting is a sales podcast for founders and sales leaders. If you are looking for actionable steps to close high ticket deals, you’re in the right place. Tune in for help with things like cold outreach and qualifying inbound leads. We regularly feature guests and experts to take our business to the next level. Pipeline Meeting is hosted by Harris Kenny, the founder of Intro, a company that provides sales as a service.

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Harris Kenny:
If you feel alone managing your business’ sales pipeline. Welcome. Consider this your invitation to join me, Harris Kenny, for a regular sales pipeline meeting, we’ll discuss finding new business and pricing, cashflow, things like getting ghosted, winning proposals, new technology, and a lot more brought to you by intro CRM.

Episode Overview

Harris Kenny: (00:40)
The theme of this episode is selling to people you know. I’m going to talk about some of the most frustrating and also the most rewarding parts of doing business, especially early on with people who you already know. Maybe these are colleagues from a past employer. Maybe these are relationships that you’ve built over the years in an industry before going out on your own, could be family members. And I’m just going to share a couple of anecdotes about some experiences that I’ve had there. These can be some of the fastest deals to close, and these can also be some of the most frustrating deals. Before we get into that, I want to tackle the tools part of this pipeline meeting, where we talk about the tools that you use to grow your business. And the first tool that I want to talk about is Transistor.

Supporting Independent and Bootstrapped Companies

Harris Kenny: (01:27)
This is the first in a series of episodes I’m going to do about a couple of different SaaS products that I’m using to build Intro CRM. Transistor is a podcast host, and it is a great one. I have been using transistor for Pipeline Meeting, and I have to say that I’ve used others and it is definitely better. It does a few things, I think, particularly well and that I’m going to touch on here.

But first I just wanted to say that I really like the company. And when you start your own business, you get to choose who you work with. And I’m really happy to choose, to be working with the folks at transistor, by, you know, using their service to host this podcast. I really like the founder, Justin (Jackson), who I’ve had a chance to connect with online. And I think that the business model and the way that they’re being independent and bootstrapped is really sustainable. I would like to see more companies like that. And so, you know, first and foremost, I’m really happy to support them in doing that, but that’s not enough, obviously the product itself needs to work too.

Why Should I Use Transistor for Podcasts?

Harris Kenny: (02:30)
I’m just going to share a couple of the things I like about it. And the first is that the interface is beautiful. When you host a podcast on Transistor and you want to embed it somewhere else, the player that they give you out of the box is really pleasant. Really nice to look at. And the backend is just as nice when you are managing the administrator panel and you’re going through these really easy single-click or maybe abbreviated steps of distributing your podcast, that whole process looks good and it’s easy too. And that brings me to the main reason why I think Transistor is worth looking at, and you may not know this if you’ve never done a podcast before. But getting your podcast out there is actually harder than it looks.

Harris Kenny: (03:12)
Podcasts use RSS, which is the old format that was used with blogs—and is still used with blogs. But recording is just the first step, right? So you can buy your recording equipment, choose the editing software, and then you publish it in an RSS feed. And Transistor’s got a post about how to start a podcast. I’m going to link that in the show notes, but you’re just beginning. I mean, if you do that, you’re basically talking yourself and then anybody who you send the link to—for the RSS feed. If you want to submit that podcast to Apple Podcasts, Spotify, Google Podcasts, Breaker, if you want to get it featured in players like Overcast, you are going to need to distribute that podcast. And when you go through the process, it can be very manual where you’re going to all these different websites and doing lots of specific individual steps to authenticate and verify that you own the podcast and publishing it through them and whatever. Transistor makes that super easy.

Harris Kenny: (04:12)
So that’s probably the best benefit, I think, in addition to supporting a great company and the fact that it looks good—they make it really easy to get your podcast out there. And that is the point, right? To spread the word about your business. So check out Transistor, and I’m going to show you a couple of quick updates about intro CRM and the product updates that I’ve made there and why.

New Features in a CRM for Freelancers and Solopreneurs

Harris Kenny: (04:31)
So I’ve got a lot of people testing the product now. Well, a lot is a relative term, but I’ve got a lot of people testing their product now, and I’m getting more feedback, I’m having more conversations. And one of the things that I’m realizing is that, you know, early on you may count your deals in different ways. So not every person thinks of their business. In terms of revenue. You may have a goal for how many units you’re trying to sell, or maybe you want to track your hours, your billable hours, that you’re booking and billable hours per client per month, you know to figure out how much you can book for your, you know, total bandwidth, total capacity.

Harris Kenny: (05:09)
So I added a new measure of value. This is now a configurable part of intro CRM where you don’t just have to do revenue. You can instead track your deals in terms of hours or units. Now this is a single setting across all of your deals and it’s configurable just like currency is, or the thousand separator, which I implemented after having some folks who were in Europe and wanted a different way of visualizing their deal values. And so it works similarly in the account menu. There’s also a new date format, which is I think more legible, you know, it shows the month spelled out the first three letters of the month and the day, and then the year. In this case Nov for November or Dec for December, that’s the default date format, but there’s still the European style where the day is first and then the month and is the US style where the month is first and the day. And then there’s the ISO standard as well. So that’s configurable.

Harris Kenny: (06:07)
And again, this is a broadly accessible tool for freelancers and for early stage founders, solo entrepreneurs. So, you know, the idea is that this is going to be configurable to meet needs and that different businesses look very different early on. And so I want that to be something that you can really have control over when you’re using Intro CRM. And finally, there’s a bunch of little improvements for mobile responsiveness and UI, some accessibility improvements well for vision impairment, and then some backend refactoring that users honestly are not going to notice, but it just makes the app easier to manage, as I’m introducing some new features. So staying busy with Intro CRM, for sure. Now to the theme of this episode, which is working with people, you know, working with those close to you.

Getting Your First Customers

Harris Kenny: (07:01)
If you have an idea of starting your business and you’re writing down these initial clients, and I remember doing this when I was taking flights, working for other people, doing business trips and thinking I really want to be working for myself. And these are the people I could be working with. And these are my potential clients and writing all those ideas, literally down on airplane napkins and thinking about it and thinking about it and thinking about it. And the chances are that you are going to have people on that list, who you already know. I think that’s almost certain.

Harris Kenny: (07:32)
This can be the fastest way to get a deal because these are people who know you super well. This can also be the slowest way to get a deal because they know you super well and maybe they want to work with you, but it doesn’t actually make business sense, or they want to work with you but they don’t feel comfortable paying your rates because whatever reason they may have, and you don’t feel comfortable lowering your rates, but you want to work with them. So there can be a lot of challenges associated with these opportunities when you know, people, uh, working with family members and things like that. I just wanted to share two recommendations for this, because I don’t want to say don’t look here, especially if you’re trying to get some early traction, there are great stories of early deals there. So I don’t want to say, don’t look there.

Tips for Working with People You Know

Harris Kenny: (08:22)
You should look there. You should look in this area of your life to help get your business off the ground. Um, but two rules of thumb. First, don’t wait too long. Apply the normal standards that you would apply for how long it takes to close a deal. And if things are dragging out too long, move on, don’t end the relationship with the person, but don’t expect that that deal is going to close. You can’t just, wait, wait, wait, wait, wait around. If you are really trying to get started, you need to find people who are willing to pay you. And if that is not people you know, from the industry that you were in before or former suppliers, or even family members or friends, then you need to just keep looking for the people who are willing to pay you. That waiting is a luxury that you likely cannot afford.

Harris Kenny: (09:12)
And then the other one is don’t take it personally. I have a prospective client right now. I’ve known people that have worked at this company for over five years. And they’re great. I know a lot of people there, but the company moves slowly. I know they move slowly because I’ve worked with them in lots of different ways, in lots of different projects. Fortunately, I’m not expecting this project. I’m pretty busy working on, and bootstrapping Intro CRM, but I would like this deal if it worked out and that would be cool. So I’m staying engaged and somewhat regular following up and seeing if this is a project they still want to do, but don’t take it personally if things don’t work out or if things are slow. Again to the first point, just don’t bank on it and move on if you need to move on, but don’t take it personally.

Harris Kenny: (10:07)
If it doesn’t work out, um, that crossing that bridge between a personal and a professional relationship, it can get complicated. Um, since it’s not personal, I recommend keeping it professional, still holding your standards around contracts. And when they pay you how they pay you, holding your standards around your margins, maybe you can give a little bit of a leeway in some specific area, but you really want to treat this like a business arrangement and you want to pay promptly or be paid promptly. And I think if you do those two things, you can navigate this a little bit better and I would not recommend overlooking this. I think this is an important way to get early clients. So don’t overlook it, but know that there are some downsides as well as the obvious upsides, which is that you are tapping existing networks of people who you probably can help because otherwise you probably wouldn’t be talking to them. If you’re dealing with something like this, let me know. I’m curious what your experience has been. And I really appreciate you listening to the show. I’m going to be pretty heads down over the next few weeks. There’s a lot that I’m working on shipping in Intro. And you know, I’m honestly very relieved that it is 2021 coming up because this year has been very long.


Harris Kenny:
Thanks for listening to Pipeline Meeting. The theme music is by Neighborhood Vandal and is shared under a Creative Commons Attribution—or CC BY—license. To learn more, read the show notes, and continue the conversation, visit