An Interview with Robbie Tripp


Credit: Robbie Tripp
Today I have a post that I am really excited to share with you! Two of my biggest inspirations on Instagram and people who consistently produce great content are Robbie Tripp and his wife Sarah, so when I got the opportunity this week to interview Robbie to find out more about his life as a creative entrepreneur, I jumped at the chance! 

For those of you who aren't familiar with Robbie, he is a writer, author, public speaker and entrepreneur living in San Francisco. He published his abstract manifesto 'Create Rebellion' in 2015 aiming to inspire creative minds and has also spoken on a TEDx talk about 'Why Millennial Narcissists are Changing the World' (Watch here!). As well as being a driven and passionate creative, Robbie supports his wife Sarah with her fashion, body positivity and lifestyle blog Sassy Red Lipstick (Check out the financial success story of Sassy Red Lipstick Here!). 

I hope you enjoy reading more about Robbie and how him and Sarah have built their empire so far! Check out the interview below!

Credit: Robbie and Sarah Tripp

It seems that your career consists of countless roles, therefore if you could describe your job in just one sentence, what would it be?

Entrepreneur! After all, that’s essentially the definition of an entrepreneur: one who wears many hats. On any given day my job requires me to be a writer, photographer/videographer, editor, web designer, social media marketer, contract negotiator, and the list goes on. The mark of any entrepreneur is someone who becomes a jack of all trades in order to build their ideas.


In the beginning of your book ‘Create Rebellion’, you give an insight on your personal creative processes and how they unfold - how often are you driven to write and create and what inspires this creativity?

I’m inspired all the time! And that’s really the point of Create Rebellion: constantly seeking inspiration and expressing yourself. It’s important to watch good films, listen to inspiring music, read great books, and expose yourself to art of all kinds. That’s what will stir the creative winds inside you and lead you to produce magic!


You’ve spoken in the past about common ‘What Ifs’ that creatives fear such as fear of failure, criticism or going unnoticed. What advice would you give to someone too scared to pursue their passions and create their own rebellion?

Great question. Anxiety is such a big problem among Millennials and a lot of it comes from social media and the fear of being ridiculed. My advice is really the only advice there is in these situations: just do it anyway! You’ve got to realize that you’ll never fly to great heights if you’re too scared to leave the ground. There is always a risk in any creative endeavor and you just have to learn to embrace that. Ideas won’t build themselves, you have to go out and make it happen. Betting on yourself is the best gamble you’ll ever make!


It’s almost a given now that as a social media influencer you are going to come across ‘trolls’ or be a part of some kind of ‘social media hate storm’. In these situations how do you stay positive and not get overwhelmed by it all?
(See articles about Robbie and Sarah's viral posts here and here)

I’ve had haters throughout my life because I’ve always been very confident in myself and my talents. I have a clear vision of what I want for my life and that type of self-assuredness can turn certain types of people off. In these cases, I just remind myself that what I’m doing is trying to make my dreams a reality and if someone has an issue with that, I feel sorry for them because they must not have any dreams of their own. It takes a very sad and insecure person to try and bring down positive people. If you ever get down, you just have to remember that it’s not you, it’s because haters secretly hate themselves.


When you dropped out of college to pursue a different path, did you have a set goal for your future? If so has that goal shifted or changed in any way since then?

I always had a vision of the bigger picture. For me, I knew that college was just a waiting room until I created the right opportunity for me to pursue my passions. I didn’t know specifically what I would do, but I knew it would involve being creative for living. That was my main focus, so I worked hard on developing a skillset in writing, Adobe Creative Suite, web design, photo/video editing, etc. When the right moment presented itself, I took it and never looked back. There is nothing wrong with going to college but for any artistic or entrepreneurial-minded person, I would encourage them to really focus on what they want and if a classroom can provide that for them. I find that the answer to that is most often no. In a creative field, the only worthwhile education is experience. Get out there and DO.


As a millenial generation we can’t seem to escape social media, therefore how do you think people can better utilize platforms such as Instagram or Twitter to build their careers?

Social media has indeed changed the game forever! Anyone can create their own career and customize their own lifestyle if they’re willing to put in the work and have something special to offer people. It’s all about personal branding and putting in consistent effort. Use social media to promote yourself, network, and connect. Social media is an invaluable tool that can literally change a person’s life overnight. It rarely works like that, but my point is the power is there. Put your creations online, promote yourself on social media, do it consistently for years and you’ll be amazed at where it can take you.


You and Sarah certainly live the dream on your social media, and it’s clear that you both work exceptionally hard to get to where you are today. What is a typical working day for you both as a creator’s / Influencers that we might not see on Instagram?

Yes, we’ve worked very hard since launching Sassy Red Lipstick in 2013 and feel very blessed to be in this position. That being said, it’s not always glamorous like it seems on social media. A lot of days we are on our laptops/phone from the moment we wake up until we can barely keep our eyes open late at night. There are so many emails, photoshoots, events, flights, etc. that make the day-to-day pretty hectic. That’s just part of the grind though. They say that entrepreneurs are people who work 80 hours for themselves so they don’t have to work 40 hours for someone else. It’s so true. The lifestyle we have is amazing but it comes with a very specific kind of sacrifice!


What has been one of the best opportunities you’ve received that has come from being a self employed creative?

I would say the travel opportunities we get always bring the type of moments where I think to myself: “I can’t believe this is actually our life/career.” I always knew I would be successful but it’s still quite a pleasant surprise when you realize you’re actually getting paid to have luxury experiences and once-in-a-lifetime opportunities. It’s hard to narrow it down to one but opportunities that stand out in my mind are becoming friends with Iskra Lawrence while creating content in New York, taking an all expenses paid trip to Costa Rica with JW Marriott, and getting courtside seats from Rakuten to watch the Golden State Warriors at Oracle Arena.


And finally, as somebody who is also lucky enough to have someone supporting my creativity (and taking way too many ootd photos!), I’m curious to know how you and Sarah separate your everyday relationship from ‘work’ and creating content?

So glad to hear you have found someone like that! I love meeting couples who support one another creatively. It makes me sad when I see husbands/boyfriends that are completely disinterested in their partner’s creative endeavors. This is a great question and one Sarah and I discuss frequently, because as an entrepreneur you can’t really ever turn it off. When your livelihood is completely dependent on your work, you have to keep pushing well beyond the 9-5 schedule. Often times, Sarah and I can burn out by doing too much for too long and that’s when we have to take a step back and remember to be husband and wife, not just business partners. It can be hard working with your significant other because it presents unique challenges but it is also incredibly rewarding. My advice here is to make a pact together to put away your phones in the evening, dish a bowl of ice cream, snuggle up in bed, and watch your favorite show together. You have to make time for your relationships as much as your business. After all, love is the most important thing in the world.

Credit: Robbie and Sarah Tripp
I hope you enjoyed learning more about the reality of being your own boss and pursuing a creative career! I would like to thank Robbie for taking the time out of his busy schedule to answer my questions and I urge you all to go and check out him and his wife, Sarah (links below)! Be sure to share this post if you found it interesting and if you would like to get in touch, feel free to email me or contact me via my Instagram, @sophie_hodgsonx!

Lots of Love,
Sophie x

Robbie's Instagram: https://www.instagram.com/tripp/
Sassy Red Lipstick: http://www.sassyredlipstick.com/

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