The Ash Holes

It’s that time year! We’re bringing our The 2025 Cigar Holiday Gift Guide to you. The perfect list of the must have cigars, accessories, and sets that the cigar lover in your life will love or maybe something to treat yourself!

In the spirit of the holiday season The Ash Heels have invited the boys to the show for this week! Let’s talk about how Ash Heels has been & if we think the boys got the contenders list right!

It’s The 2025 Contenders Show!!! We name the 6 contenders for 2025 Cigar of the Year, along with some honorable mentions that didn’t make the cut.

The warnings are over… the cigar crisis has officially hit the industry. In this episode, we break down what’s really happening behind the scenes as manufacturers struggle, retailers feel the pressure, and the post-COVID boom becomes a distant memory. Are we witnessing a repeat of 1998’s industry collapse, or is this downturn temporary? We dig into the data, trends, and insider conversations shaping the future of premium cigars.

This week we're celebrating the 9th Anniversary of the Ash Holes! Lets look back on almost a decade of the Ash Holes and predict where we'll be by next year's show. Can we make it to a decade of shows!?

Lets Talk about our favorite cigars! The guys have talked about what their favorite smokes are in the past but the Ash Heels will let you know some of our favorite cigars to enjoy all year long!

This week we’re talking smoking cigars internationally! Dan is in Ireland right now looking for cigars. What’s the best way to enjoy cigars outside of the US? Bring your own or find something new from Cuba etc!?

Dave interrupted our plans today, and gave his honest review of Dan's wedding. How was the music? How was the food? Was it fun? Find out, and a listen for an early preview of our upcoming contenders list.

This week we’re talking wedding cigars strategy! Dan’s getting married this Saturday & breaks down all the things you need to have a perfect cigar wedding experience from groomsmen gifts to cocktail hour!

Lets talk about some of the things we wish we knew about the cigar world before getting into the hobby! What could we tell someone who’s new to cigars what pitfalls to avoid or things to keep doing from being a beginner to becoming fully into the culture!?

This week lets see if there’s been a shake up in Cigar Maker Power Rankings, who are the top players right now in the cigar world!?

This week lets talk about what’s better for a cigar brand? New Lines or limited editions? Companies are having success right now using each method but which will work in the long run?

The 2025 New England Cigar Expo & Two Guys 40th Anniversary Party is over! Lets talk about how it went & what each of our experiences were since we all did different things throughout the weekend.

It’s here! We are just 3 Days away from the 2025 New England Cigar Expo & Two Guys 40th Anniversary Party! Lets talk about what you can expect if you’re joining us this weekend for the sold out event & what we’re most looking forward to!

The Ash Heels are back to make the perfect cigar kit! Lets Talk the perfect tools you’ll need for a perfect smoking experience: Butane lighter, V or straight cutter, travel humidor, proper humidification devices.

This week on The Ash Holes, Labor Day is right around the corner! Let’s talk about the perfect cigars to light up this Labor Day Weekend!

This week we’re playing What IF? Two Guys Edition! Dan has a series of questions for Dave about key moments in Two Guys Smoke Shop History & we’ll discuss what could have happened if the timeline was different!

This week we are joined by Ed Santamaria, buyer at Two Guys Smoke Shop. Two Guys may be celebrating it’s 40th Anniversary this year but there's another special Two Guys Milestone to talk about as Ed is celebrating his 30th year working for the company!

This week on The Ash Heels the girls chat with Mel from Elevated Humidor! Let’s talk about her origins into the cigar world & what’s it like owning her own cigar store!

This week we’re going to give you the secret, or secrets, to making a perfect cigar. Dave’s not here to weigh in but we’ll tell ya our perspective on what is needed to make a perfect cigar successful!

Today we ask who’s your Cigar Starting 5 if you were to start a “Cigar Team” and had to pick 4 other people to lead you to success who would it be & why!? Could be anyone from master blender, corporate officer, spokesperson, or cigar roller! No wrong answers here!

With the Padron Ruby Red Exclusive Edition Release Around The Corner we ask why make a great cigar once?! Sometimes a cigar comes out & it’s a big hit then its never to be seen again. Why do manufacturers do this? & what could change it for the future?

Summer is in full swing, lets talk about the new hot cigars of the summer 2025 & what’s still left to come out this cigar smoking season!

We’re smoking Outcast Cigars this week so it’s a good time to ask are Women Outcasts In the Cigar Industry?? Times have changed & there’s lots of women involved in all aspects the business from stores to Corporate Leaders but are the challenges still the same for women in the industry?

2025 has been a very different year for cigars than last 5 & it’s time for cigar retailers to work on better strategies for this year & we’re here to help!