Jeremy Chatelaine is the founder of Quickmail.io, a tool to help businesses generate leads on autopilot with automated outbound emails and smart follow-ups. Quickmail.io is one of the first companies to provide a solution for sales automation. In just two years since inception, Jeremy grew Quickmail.io to over 1,000 customers and over $50,000 in monthly recurring revenue.

In this interview, Jeremy breaks down each phase of growing his business, from validating his idea to his first customer acquisition to hiring his first team member. He also shares his insights on the realities of a having the freedom of choice with your lifestyle business, and why chooses to focus on customer experience over massive growth.

In This Interview I Ask:

2:30 - Why did you decide to become an entrepreneur?

3:34 - What problem did you build Quickmail.io to solve?

4:41 - What did your process look like to validate the idea?

5:42 - Can you give us a sense of where Quickmail.io is right now in terms of monthly revenues and customers?

6:35 - What was it actually like for you to get your first customers?

9:42 - When you first experienced this problem for yourself, did you initially go see if there was something out there to solve it for you?

10:57 - When did you make the shift to focus on Quickmail.io as the business [you’re] going to build?

12:05 - Where were you finding those people [to have one-on-one sales conversations with]?

14:25 - How many sales conversations would you say you had? When you were doing the one-on-one sales conversations, how long did you do that?

15:38 - Once you switched from having one-on-one conversations, what was the primary way that you were acquiring new customers?

16:25 - Roughly what dollar amount, on a monthly basis, did you grow to [during the period] you weren’t really focusing any specific marketing effort?

19:20 - What sort of things are you looking for that would cause you to advise someone it’s time to leave [their] job?

21:42 - What is your most successful channel for customer acquisition? What is the number one factor that drives growth for you over the past couple of months?

23:45 - Have you thought about, [in] three years, what Quickmail.io would look like? Do you have a vision in place for what you want Quickmail.io to be?

24:45 - What was just one thing you personally needed to work on or overcome to grow Quickmail in the way that you did in the last two years?

28:48 - Have you put together any team?

31:13 - What does it look like for you to run a $50k/month business? What do you do on a daily basis?

35:44 - Who is an entrepreneur you admire?

36:30 - Is there something that you do every day in a ritual type way, no matter what?

39:21 - Who was your hero growing up?

41:47 - You’re going to a desert island and you can only bring one book, what book would you bring?

When to Quit Your Job

When you know for sure that if you spend more time on your business and it will equate to more sales, then you can quit your job. If you leave before there’s a predictable path to more customers, you’re gambling with your future and your family.

The Freedom to Choose When and When Not to Work

Many people build a lifestyle business to have the freedom to choose when and when not to work. However, sometimes you may need to force yourself to work, even when you don’t want to, in order to get things done. Other entrepreneurs who only work when they “feel like it” end up not doing much for their business. A business is like a child. It needs to be fed and changed. There are a few things that you just have to do. It’s not always sexy, but just do it.

How to Choose Your Mentors

Have mentors with the skillsets you wish to acquire.

Show Links:

Quickmail.io, website

Quickmail.io Job Opening for Customer Support, apply