We caught up with the brilliant and insightful Pretty Sister a few weeks ago and have shared our conversation below.

Pretty Sister, looking forward to hearing all of your stories today. We’ve love to hear an interesting investment story – what was one of the best or worst investments you’ve made? (Note, these responses are only intended as entertainment and shouldn’t be construed as investment advice)

well. as an artist or any kind of creative. Its almost imperative that you make investments. For me its been basic things needed for my work, computer, microphone, instruments, lessons. Even if its a keyboard that is expensive but unlocks some creativity for a period of time. good investment. when i think on all of those, in the end i dont regret any tour ive ever done, or any peice of gear purchased even if i lost money…but what i do sometimes regret are the bad investments. and those all tend to be people. be very careful who you invest your time into. wether it be romantic relationships, managers, band members, whatever…those are the ones i go “dam, yeah…if i could go back i would probably be better off if i didnt give that human all of my energy and time for that year or in some cases way more than that. as a self employed creative it’s VERY difficult to sustain not only your bank account, but your mental health, INSPIRATION and work-flow. my biggest regrets on investments all come from bad investments in other humans. be careful with who gets access to your time and energy. im writing this down to remind myself haha.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I started off singing in my bedroom, then joined a band in high school. that band became another band and we toured and practiced and worked our asses off. that lead to a record deal with motown and then subsequently turned into a publishing deal for my own music but to also lend my hand in writing and eventually also producing for others.

i think because i come from the band world, it gave me alot of experince working on creative with others. Writing music is very specific and very personal so its a very delicate dance. you have to be able to work with egos and emotions and be able to communicate your own ideas while hearing others and manage your own ego. i think its beautiful and one of my favorite parts of being a producer and co-writer on other projects. I LOVE when someone has a better idea than me or a better idea than the last person. it brings me relief, it excites me and you can also feel the same from everyone else in the room.

with my own music, i push myself to be honest and talk about things that maybe dont get touched on so often. like if ive heard it before then what is the point of this even existing? is there a more simple way or maybe a better metaphor that will hit a person even harder? and theres caveats to that for sure. like how often have you heard the same uplifting message in a dance song? BUT BUT BUT does the music behind it make it hit different, is it evoking the same feeling but with something fresh and at the end of the day does it fucking FEEL good!? those kinds of things need to exist and sometimes the best way to do that is to just be basic…again…a delicate dance.

Can you share a story from your journey that illustrates your resilience?

oh man, well. i’ve been here about 15 years so that alone will say alot. Ive lost band members, record deals, managers and publishing deals. worked sometimes 3 jobs at once trying to support my music career. but ive never stopped. even through all the lows and rejection i just ignore it. all the negative self-talk and depression is sometimes unavoidable but i just somehow just act in spite of it. maybe im crazy ignoring all of these signs to quit. but im just fucking crazy and i wont. ive become great at beating a dead horse. Theres always a little bit of hope. Some breadcrumb that leads to something telling you “you’re not a phsychopath” and your doing the right thing. or maybe i am? at this point i dont know. but ima keep going…

How did you build your audience on social media?

for someone just starting in music my best advice is to start a band. if you’re a dancer have a crew. if you make videos have a collective of sorts. the point is to partner with like minded driven individuals and build a community around you. especially starting out, the the support and built in network really helps keep you not only motivated but accountable. for example you as a solo artist could maybe pull 10 family and friends to your show. but with another 4 members they each do the same. damn, now all the sudden you can pull about 50 collectively and now you can grow from there. and if you have the opportunity to be on television take it. theres still nothing besides making friends with taylor swift that will help grow your social media more than that. so if theres a singing contest show. do it. your ego might tell you its below you…but its not. its free content, and also millions of eyes that don’t have the option to scroll right past you. its analog baby. they have to watch and if you’re good, they will follow and best case scenario become a longtime fan or friend.

Contact Info:

• Website: https://linktr.ee/prettysister
• Instagram: @prettysistermusic
• Facebook: https://www.facebook.com/prettysister/
• Twitter: https://twitter.com/prettysister
• Youtube: https://www.youtube.com/@PrettySister/featured

Image Credits
FIRST ROUND : https://www.instagram.com/_johnchong/ 2nd round (4 pics) : https://www.instagram.com/zacpoor/?img_index=1