Will McQuain is an entrepreneur and founder of Good Cigar Company, a web-based cigar delivery service that combines great design, approachable packaging, and curated products for a modern, occasion-based cigar consumer. He began his company last year after the social payment startup he worked for was acquired by Airbnb, and he decided to take the opportunity to try something new. Still in its first year, Good Cigar Co. has already exceeded expectations, generating more than $170,000 in revenue, with more growth on the horizon.

Will says that, particularly when he was first starting out, he relied heavily on Skillshare to develop new skills and brush up on old ones. He says he has “probably something like 50 or so completed classes” now, and believes that they have been an integral part of his company’s success. We chatted with Will to find out more about his business journey, the advice he has for fellow entrepreneurs, and how Skillshare helped him realize his dream.

Will McQuain, Founder, Good Cigar Co. 
Will McQuain, Founder, Good Cigar Co. 

Hi Will! Let’s start from the beginning. Can you walk me through what Good Cigar Company is all about?

Sure! Happy to. So about two-and-a-half years ago I was working for a startup in San Francisco, TIlt, that was later acquired by Airbnb. While I was there I was working on a crowdfunding product and watching a lot of other people start a little fledgeling brand, come up with a prototype, and set preorders for it. I would watch these little success stories go from zero to maybe 100k-200k in funding, and from the sidelines was salivating at the idea like, man, I would love to do something like this.

I have always been a big fan of cigars. I was always the guy who would bring cigars to a bachelor party or a golf trip, and every time it was a huge hit with the guys in the group. Cigars can be intimidating and complicated and require a lot of gear, [but because] I was the one introducing [them] to people, I found that when someone was there to walk through it, it could be a really fun experience. There are a lot of similarities with things like wine, craft beer or craft spirits.

I kept expecting to see something like Good Cigar Co. come along, but when it [didn’t], I started doodling around the idea. Tilt was eventually acquired by Airbnb, and I had this moment to accept a job at Airbnb or go full-time [building Good Cigar Co.]. It was way too early for me to go full-time, but I thought it would only get riskier for me in a couple of years so I made the leap about a year ago. [Good Cigar Co.] is my full time job, and there are three other part-time people that help me with photography and legal stuff.

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I understand that Skillshare has been a big part of your entrepreneurial journey. How did it help you get to where you are today?

I found Skillshare through early explorations around logo design and branding. When I came  upon a class about designing a brand system, I was just really taken with it. I knew when I started my business journey that there were things I was going to be good at; all of my jobs [had been] about getting people to come to a website and make a purchase. But I was not a designer at all, I’ve never done any kind of branding or visual design, and I realized that Skillshare was this amazing resource for me. Every step of the way, I’d be like ‘I have an idea [of how to do this] but need to brush up on it.’ I guess I probably have something like fifty or so completed Skillshare classes. It was almost like a collection of mentors for me.

Any classes that you remember being particularly useful?

I would point to a couple. There was a course on packaging design that was probably the most transformative for me. I had this idea like, okay, a subscription cigar service is interesting. There’s value there. [But] walking through that course really helped me think through the experience of the user. What do you want it to feel like when you open it? [The class] described packaging design as ‘UX for the real world’ and I thought that was fascinating. I became obsessed with packaging, running through the aisles at Whole Foods and being like, ‘there’s a reason that they did this, or this, or this.’

[Our packaging] is a competitive advantage for us.Not just the way it looks. It’s very Instagrammable. Loud. But also, it’s a big competitive advantage for us to be pulling all of these things together [into one packet]. One of the many reasons why people aren’t into cigars is, you need a lot of gear. You need cigars, something to keep them humid, something to cut with, something to light with; four things you need to have with you when the time is right. For people who don’t smoke often, for people who are just celebrating at a wedding, or congratulating a new dad, [having it] all together is really valuable.

Are there any other classes you remember enjoying?

I love the copywriting course by Alison Esposito. I think that was the only project that I did, I wish I had done more of those actually, but the reason I did [Alison’s] was because she said, ‘hey anyone who completes a project, I will review your copy.’ So I got to get her feedback, which was really exciting.

Mailchimp has a bunch of great ones. I watched all of MailChimp’s.

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It sounds like you were all the about packaging, and branding, and email marketing!

Yeah, a common theme was design, branding, and marketing and they go in that order. I [also] took some typography.

I discovered in myself a love for design. It was like an itch I never knew was there. I didn’t realize I would be so into it! I am already thinking that down the road, regardless of where Good Cigar Company goes, I would love to come into the next thing from a more bolstered design standpoint. I have really loved that [part of] this whole journey.

How has diving so deeply into design helped your business grow?

I’ve been saying from the beginning that I think we are fighting an uphill battle [around] the perception of cigars and tobacco. We are aware that it is bad for you, and we are really trying to [position ourselves] as the occasional cigar company. Cigars you smoke at just a couple of things a year.  Design allows us to overcome some immediate hurdles. The design and branding gets people over that initial hump.

It pushes people to reevaluate some preconceived notions about cigars?

Or what you might expect a cigar company to look like.

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So now that you’ve been around for a year, how is Good Cigar Company going?

It’s going great! The Good Cigar Co. pack is only our first product, but we definitely have a vision towards being a big player in the cigar industry. Outside of a few names like Cohiba and Montechristo, there isn’t a lot of name recognition among people who aren’t die-hard cigar fanatics, and I’m hoping to build a brand that breaks out of that. Our mission is to make cigars modern and approachable, and we have a few exciting projects in the short-term (and long-term) pipeline to that will help us continue down that road. I like to think that we’ll have accessories, local clubs, and even our own cigar bar one day.

Do you have any advice you’d like to share with other entrepreneurs?

My biggest piece of advice to anyone who is looking to start something is: Do it. Don’t wait until you are ‘ready.’ There has never been a better time to build something and share it with the world. Stop making excuses and just start!

Also? Don’t worry about being secretive with your projects. No one is waiting to steal ideas, and you’ll need the feedback that comes from showing people what you’re making. There’s a quote by Reid Hoffman, founder of LinkedIn, that says “if you’re not embarrassed by the first version of your product, you’ve launched too late.”

Skillshare has (and continues to be) an incredible resources for me to learn about how to build and grow this business, but I learned the most by taking a leap and launching way before I was truly ready.

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You can learn more about Will McQuain by visiting his Skillshare member page, or by following Good Cigar Co. on Facebook and Instagram.

This interview has been edited and condensed for length and clarity.

Written by:

Rachel Gorman