Comedian Finances with Ashley Gavin

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Comedian Finances with Ashley Gavin

If you’ve been listening to the show for a while, you know that I love to profile people with all different types of jobs, whether it’s through the Naked Sessions or individual episodes. I think we all learn so much from walking in someone else’s financial shoes and understanding how they make their decisions. Today, I’m excited to profile Ashley Gavin, comedian, writer, and actor. I’ve honestly been curious about professional comedian finances for years now and really enjoyed learning how Ashley has made a full-time career of this.

What are we drinking?

Ashley - Black Coffee

Shannon - Black Cherry Schweppes

Podcast Notes

  • Ashley is a comedian. She has always wanted to be an actor or performer her whole life.

  • She worked as a software engineer for a while, she was in a relationship, and lived in a nice apartment in Boston, and she was unhappy. She was avoiding the thing she had always wanted to do.

  • She knew immediately when she left college that she was on the wrong path, because she wanted to do something creative.

  • Ashley put in for a leave of absence from her job, and she is still technically on leave. She has been working toward being a full-time comedian ever since.

  • Ashley doesn’t think she was ever really bad, at least not cringe worthy, but it was because she acted in a theater club since she was 11 years old. She knew how to deliver a joke.

  • When she tells a new joke that doesn’t work, thankfully, she has a large portfolio of things that will get the audience back.

  • You eventually transition from caring about a bad performance to caring about being good and wondering why you are not more successful. They both make you doubt yourself.

  • There is no one path to success. Early on, Ashley took a couple of comedians that had careers that she wanted and researched all of their work to figure out the path that got them to where they are now.

  • Ten years later, the path is totally different, because technology, television, and how we consume comedy has changed. It is hard to figure out how to make your brand successful.

  • Ashley started out pretty successfully, but then plateaued. Comparison is difficult to avoid, because everyone in her industry is on stage and online.

  • Ashley left her job and has been a comedian for six years. She was very ambitious when she first started and she had heard, about six months in, that you could apply to conferences of college students and the college students would book you.

  • She grew up in New York, and when she started doing comedy she was working full time, living with her mom, and saving a lot of money, knowing full well that what she saved would be the bedrock for her career path.

  • Ashley applied to the conferences and she booked a ton of them. She realized this is how she could make comedy her career. She focused on colleges and also investigated other options, like cruises, corporate gigs, teaching comedy, etc.

  • There are disadvantages, however, because doing work like this takes you out of the scene and removes you from networking.

  • For the most part, her performances since late 2015 have been mostly colleges, corporate gigs, and cruises. She quit her day job in early 2016.

  • The most efficient way to make money in comedy is through a big road gig. If it is a well-funded college, Ashley can make $3,000 in one night. Corporate gigs are pretty good. When she does cruises, they pay pretty well, but if she does Airbnb for her apartment when she is gone, the money is really good.

  • When she performs at a venue in New York, she gets an 80/20 or 70/30 door deal, so she can make $2,000 or $2,500 if she sells it out, but she is doing all of the promotion. You can’t headline the same city over and over again, you need to spread it out. You have to be a pretty big draw and willing to travel.

  • Ashley has a monthly show and she makes about $300, depending on the month. If she does the show in Boston and Philadelphia, that is $600 to $700 a month, depending on the size of the venue.

  • Ashley just signed with a new manager that manages big names, but it is a small company. She dropped her old agent, because it was time to move on. She has done all of her own college booking herself, because it isn’t that difficult to learn. For the TV, film, and production side, you need a good manager.

  • Her first manager wasn’t a great fit. She worked with him for two years, but they didn’t do much together. After they parted ways, she cold called managers, but she found that the best way to find a manager is for them to find you, by being in the places they are. It took about two years for her to find her new manager.

  • The comedy industry is tougher for women than men. There are fewer opportunities and on a micro level, it takes women a little longer than men to win the confidence of the crowd. Women have to be better to get the same amount of respect.

  • People who are headlining tend to bring a different type of act to open for them, and there is more pressure for this for women and minorities. There is a subconscious thought of will it be too much if the opening act is similar.

  • When Ashley worked in tech, she had several women who were really hard on her. She has not had a lot of that directly in comedy, but she also hasn’t had anyone reach down to her either.

  • Ashley’s financial goals are secondary to her career goals. She wants to do the best comedy work that she can do. She wants to make movies and be on television. She doesn’t have any wild dreams about a beach house, she just wants to get paid well for the work she is doing. The more you make, the more you want, but that doesn’t correlate to happiness.

  • Many of The Financial Gym clients don’t necessarily want to make a lot of money, they want to do work they enjoy and manage their money well. Shannon finds that a lot of women feel bad if they don’t want to make six figures.

  • Ashley is a regular on a roster of cruises and she is getting ready to launch her own podcast, and her next financial goal is to really afford the apartment she lives in, because when she left her tech job, she didn’t give up her nice apartment.

  • She still has a fear of going back to a day job. She would like to be comfortably where she is now as opposed to kind of comfortable.

  • Ashley used to have fear about running out of material, but inevitably, she writes something better. She is more afraid of becoming irrelevant and not understanding the internet, not understanding the culture, and staying up to date.

  • Ashley does social commentary, and she is beginning to get the feeling that to some people she is too conservative. People are starting to assume Ashley doesn’t understand. Before, they assumed she was liberal and she understood what was going on in the culture. She has to change and stay up to date to keep going.

  • On the cruises where the shows are PG, she can’t say that she is gay. The cruise gigs have shown Ashley how divided we are as a country.

  • Censoring herself on the PG shows is the best way to have a good show. Her talking about being gay in a comedy show isn’t going to change someone’s opinion on the subject.

  • Ashley will edit a set based on what she thinks the audience will like. She just wants to make people laugh. She is mostly looking at what people will laugh at. She has fans who like everything, but when you are not a household name, you don’t have the luxury of performing in front of people who are there just for you. She doesn’t hate any of her material.

  • Ashley makes a note in her notebook every day, and she tries to write more in bigger blocks of time by looking back at her daily notes, probably once or twice a week.

  • An hour show is typically what she does, but she has gone up to an hour and a half. People get tired and more than that is too much. She writes a set list with a list of the jokes on them. When she does the same show, she starts to remember it. She glances at her list whenever she takes a sip of water.

  • Ashley doesn’t usually have difficulties remembering the jokes when she is on stage.

  • If someone is thinking comedy is what they want to pursue, Ashley is an evangelist on going for it whatever the risk. You can always recover and go back to what you were doing before.

  • Her advice is to consider yourself a professional from the moment you begin. People Ashley has seen succeed, are those who respect themselves as a professional. No one will respect you at first so you have to be the person who does. If you are experimenting, you are going to let yourself off the hook.

Takeaway: My biggest takeaway is that you can make any career work financially, as long as you have a plan and a passion for it.

Random Three Questions

  1. What’s the worst you have ever bombed, and did you ever feel like quitting?

  2. When people say, “Tell me a joke”, what is your response?

  3. If this was your last night on earth, what is your last meal?

Connect with Ashley

Website: ashleygavin.com

Instagram/Twitter: @ashgavs

If you have any topics you would like me to cover on this podcast, or If you’d like to get in the financially naked hotseat, I encourage you to email me to Shannon@fingyms.com, or join the private Martinis and Your Money facebook group, and let me know what you want to hear.

if you’d like to talk to my team at the Financial Gym to help you manage your finances around your career choice, I hope you’ll reach out to us. My trainers have literally seen it all and don’t care how you got into your financial situation, they just care about getting you where you want to go. The great news is that Martinis and Your Money listeners get 15 percent off Financial Gym services. So head over to, or send friends to, financialgym.com to get set up today.

Shannon McLayComment