We had the good fortune of connecting with Conner Cherland and we’ve shared our conversation below.

Hi Conner, what was your thought process behind starting your own business?
After graduating college at the University of Santa Barbara in 2014, I worked at a tech company called Appfolio for two and a half years making websites for property managers. Most days I would work 7AM-3PM, bike back to my house, and write a song before going to bed. I planned to write 40 songs in 6 months, and got pretty close to that goal. During those years I moonlighted as a musician in town playing bars, wineries, dentist office grand openings.

At a certain point I went from one gig to three gigs per week, and this really started to tire me out. My schedule got so packed that I gave my fiancé my Google Calendar password so that she could put herself onto my calendar and we could spend time together. My boss at Appfolio wanted extra hours, and I was turning down gigs because I was already maxed out. I burnt the candle at both ends and needed a more long-term solution.

In 2016 I had a long phone call with one of my dad’s friends. He asked me about why I wasn’t investing my savings into my 401K, but not in the “I-know-better-than-you” kind of way. I told him I wanted to be a musician, and he laughed and said something like “It sounds like you’re making plans to quit your job, and you’re saving your money. It makes sense. You just haven’t told your dad yet!” Granted, I hadn’t told myself yet.

The conditions were right: I gave my parents a powerpoint presentation about why I’d survive as a musician (a very popular persuasion tool in the tech world), my fiancé was on board and had a steady job, I hit my savings goal, and I almost had enough gigs to make rent. I quit my job and with the blessing of my coworkers, family, and friends started a new chapter.

The point of this backstory is that a part of me wanted to be an artist, but wasn’t always aware or comfortable around that idea. I didn’t know it at the time, but my actions were drip-by-drip creating the business I’ve run for the past five years. I started this business when I was 24 because I knew the decision to quit my tech job would only get harder, and that my love of comfort would keep me from pursuing fulfilling work. Quitting my job allowed me to say yes to every gig that came my way, opening doors that I never would have anticipated, and finding new avenues for paid performances.

Let’s talk shop? Tell us more about your career, what can you share with our community?
Please tell us more about your art. We’d love to hear what sets you apart from others, – I think what sets me apart is that I’m genuinely not looking for fame and fortune. I’m looking to write the best song I possibly can, and not let fear/love of comfort keep me away from what I want deep down. I’m relatable and show that the full-time artist life is much more approachable than you would think. My intent is to inspire others to create and share their authentic selves in response.

What you are most proud of or excited about.
– I’m proud of my consistency and willingness to show up despite discouragement. In this industry it’s all about who you know, and because I didn’t know anyone I just started gigging wherever I could find work. This led me to know a few key people who have helped me find other gigs and pay bills. I’m also proud of my podcast as a means for me to meet other artists and have a sincere conversation of whatever they care about. One of my great treasures in life is meeting a new friend, and I’m glad to have a job that creates opportunities to meet people beyond banal surface interactions.

How did you get to where you are today professionally. Was it easy? If not, how did you overcome the challenges?
– It’s not easy (for me, at least) to make enough money playing music. In 5 years I’ve performed at over 1,000 gigs and it’s a lot of emailing, packing the car, and hunting people down for money they owe you. I overcome the challenges one step at a time. I write my goals on a piece of paper and file them under “projects” on my desk. If I don’t know where to start, I type the question into YouTube and start watching videos: “how to produce music on Logic Pro X”, and “how to check transmission fluid in Toyota RAV4”. Keep trying to make progress, however small.

What are the lessons you’ve learned along the way.
– I should be kinder to myself.
– If you hate the gig, ask for a lot more money.
– Ask good questions and people will think you’re interesting.
– Tell people what you admire about them, it’s awkward but really important.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
I’m new to LA, so I wouldn’t be the best guide in the world…but I can definitely give you a tour of Santa Barbara (where I lived the past 11 years). – Breakfast at Goodland Hotel in Goleta
– Bike ride through UCSB, ending up at the UCSB lagoon for a walk along the cliffs
– Lunch (Sama Sama) and drinks (The Good Lion) on State Street
– Shoot some pool at Don Q’s
– To-go Tonkatsu Ramen from Sachi Ramen, eating at the Mission Lawn
– Custom cocktails at Bobcat Lounge/Farm-to-Bar

You’re also welcome to use these ideas for dates, except Don Q’s…the pool scene there is a bit competitive.

Who else deserves some credit and recognition?
I’d like to give a shoutout to Christin at Logitech. Christin has continued to hire me for meetings and events throughout the pandemic, forging new paths for my career and providing consistent gigs during a difficult time. I’m not sure I could have survived the past two years without our partnership. I’m forever grateful for the luck and favor involved in working with her.

Website: connercherland.com

Instagram: @connercherland

Linkedin: https://www.linkedin.com/in/conner-cherland-391b3b36/

Facebook: @connercherland

Youtube: https://www.youtube.com/c/itsconnercherland

Image Credits
Robiee Z, Elena, Holland Chance, Layne Deyling Cherland

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