Starting a business can be terrifying. Weighing the pros and cons, the risks, and other considerations can be so overwhelming that often promising entrepreneurs stop before they even start. We asked some phenomenal entrepreneurs about their thought process behind starting their own businesses. Our hope is that by making the thought-process less intimidating we can help more folks think through whether they should take an entrepreneurial leap.

Katharine Kuharic | painter, artist

Im an artist and have been working with galleries primarily in New York for over 35 years. I started selling paintings when I was only 21 years old and never approached making them as starting a business. I wanted to make paintings that challenged social mores around sexuality ( this was in the 80s) and later to commemorate the deaths of my gay friends to the AIDS crisis. I was much more interested in being a political activist than being financially successful and always worked at crappy retail jobs to get by . Read more>>

Mark Huddleston | Wine Importer

At the time I was working as a Sales Representative for a Wine Importer/Distributor in Los Angeles. Before I had worked in restaurants for over 12 years, starting as a busboy at Chili’s and then having the opportunity to be a Sommelier at Providence and finally at Gordon Ramsay. My wife and I had just gone on our honeymoon in Bordeaux and then in Vienna. Read more>>

Helena Bowen | Speechwriter & Speaker Coach

In my early 20s, I worked on set in film & television as an Assistant Camerawoman (AC) and later an Assistant Director (AD). I loved working on set — one day I was wrangling 50 extras on a fake airplane in North Hollywood, and another I was operating an animatronic tentacle in an alien movie. But that level of freedom & creativity also came with 12-hour minimum days and a wildly unpredictable schedule. Read more>>

Jennifer Cabibbo-Amado | Licensed Esthetician & Small Business Owner

I didn’t realize I wanted to be an entrepreneur at first, I worked 10+ years in higher education and the private sector before realizing my true calling. My journey to being a small business owner started with my education. I always knew I was detail oriented, business savvy and creative so I pursued my bachelors in Business Administration from Chapman University and my Masters in Communication Management from USC. Read more>>

Ryan Carpenter | Fena Barbitall – drag superstar

Now that I’m in my 20th year of drag, it’s easier for me to look back and piece together how it all started. Originally Drag was a fun, creative exciting way to make money doing what I love. over the years beyond my control it has developed into a business. I’m still trying to catch up with that. Read more>>

Rayvon Burrwell | DJ/Event Curator

I just wanted to Have FUN forever!!!! I wanted to do something that I was passionate about, so that way, the work would feel justified & I’d be motivated. A while ago, I heard a saying that went “If love the work, and focus on doing that really well instead of the money or validation, that they would both eventually appear. And if they didn’t you’d still be somewhat content with yourself.” Read more>>

Nina Bal | Advanced Facial Aesthetics Clinician

I started my career in Italy close to 15 years ago and moved to London for family not speaking a single word of English. For the first 5 years of my London career I was doing all the jobs no one wanted to do in dentistry – ie. heavily discounted coupon teeth whitening from basement practices in the city. During this time and while I became completely proficient in English I grew a love of facial aesthetics from my background of cosmetic dentistry. Read more>>

Jazmin Olvera | Florist & Creator of Time of the Season Flowers

I received my Bachelor’s Degree in Art History from San Francisco State University in 2020 right as the pandemic struck and I had to make the difficult decision of moving back home to be closer to my loved ones. I started applying to jobs in museums and art organizations but wasn’t having any luck. Read more>>

Kevyn Lee-Wellington | Owner & Founder

Creating Fluffy’s Sno-Balls was a 15+ year dream of mine, since arriving here in California as a result of Hurricane Katrina. Having climbed the corporate ladder and ascending to the role of Vice President of Operations for US Foods; I was fed up with “Corporate America.” Read more>>

4000 WEST | Entertainment & Production Facility

4000 WEST was created out of chaos to be honest. This business was a re-vamp of an old business that needed a facelift. What better way than to create a vibey, soulful, creative space for all creators than to do it in the heart of Burbank with the intention of serving others. Read more>>

Diamond Polk | Realtor with ACME Real Estate

I’ve always been interested in real estate and was encouraged by my mom to pursue real estate after graduating from the University of Southern California. I began the process of obtaining my license which included course training and studying for my real estate exam. After tirelessly studying, I thought, I should put this pursuit on pause and live life as a carefree, 20-something year old in Los Angeles. Read more>>

Robyn Jackson | Recording Artist & Songwriter

My process is experience based. I’m a dancer first, vocalist second, and songwriter third. All of my experiences from college to traveling the world as an entertainer to even my own life experiences in relationship and business have lead me to the brand I’ve created for myself the artist RBYN. Read more>>

Christopher Gil | Founder and CEO of Optimal Sports Management

The thought process behind starting Optimal Sports Management was simple, I wanted to pursue my dream of becoming an NFL agent. By being able to recruit and work with elite high school/college and professional football players through handling their marketing efforts, I want to establish my reputation as one of the best up-and-coming sports agents in the industry. Read more>>

Christopher Still | Trumpet at Los Angeles Philharmonic and Founder Honesty Pill Coaching

The Beginning With six years of university and two degrees under my belt, I was excited to start my career. After receiving a Master’s degree in orchestral performance, I noticed that I had not been automatically offered a full-time trumpet position with a major symphony orchestra. Go gure. And I didn’t have any audition committees begging for my resume either. Read more>>

Tanisha McClain | Farm to Fork Chef, Baker and Bartender

I have always loved cooking, I wanted to share my food love with more people in a more accessible capacity. Read more>>

Amy Muller Adams | Tattooer

I started my shop out of necessity. I had just moved up from LA, looked around for a job at a shop for about a week, and wasn’t really excited about working for another person I didn’t look up to. I had just had a few really bad experiences and just wanted to keep to myself and make art somewhere on my own terms. I found a cheap commercial spot and someone to share the rent with and it just all came together. Read more>>

Edwin Benton II | Entrepreneur, Writer, Investor and Pilot

I wanted to have control and be able to do things my way without having to compromise my vision or perspective. Also, most people have to work in life, if I’m going to work I want to make sure that I am getting the most return for the time that I put in. The only way that would happen is by being an entrepreneur who can solve a major problem and then be able to decide on your income. Read more>>

William Huang | Philanthropist and STEM Education Equity Advocate

On March 11, 2020, the World Health Organization (WHO) declared COVID-19 a pandemic following a rising sense of alarm over the lethal virus spreading across the world. Although there was little initial knowledge about the virus, one thing was certain: it was airborne. Turning on the news, I was extremely troubled to hear about the continued increase in shortages of PPE across California hospitals sparked by terror over the virus. Read more>>

Savanna Ruedy | Photographer

Starting my photography business has been such a natural progression but over a lot of hard work and random gigs.. I went to school for photography at Minneapolis College of Art and Design, After that I was able to transition to internships related to photography in NYC. Read more>>

Katie Salove | Interior architect and designer

I’ve always been a highly independent self-starter and come from a line of entrepreneurs within the home and hospitality space. My grandfather founded a contracting company, my grandmother owned an antiques store, and my father started and still runs his commercial real estate brokerage and development firm. Read more>>

Klayton Carroll | Mental Performance Coach and Speaker

I started my business, Ready. Player. Win., because I saw a need in the market to provide young athletes with the mindset needed to overcome mental setbacks. Many young athletes need to recognize that mistakes are a part of the process, and that they need to find ways to conquer this fear to be disciplined players both on and off the field. I started Ready. Player. Win. Read more>>

Shaotian Cai | Actor, Acting Teacher, & Entrepreneur

I was one of the earliest international students from China who studied theatre and acting in the United States. This expereince was transformative for me on lots of levels — artistic and personal. Read more>>

Jessica Johnston | Founder & Owner

I have always been very independent with an entrepreneurial spirit. Even as a kid I liked to find little ways of making money. I remember one day, I was sitting at my desk at this big corporate job and the quote of the day came up on my computer. It was by Tony Gaskins and it said “ If you don’t build your dreams, someone will hire you to help build theirs.” Read more>>

Marie Claire Macadar | Artist-Musician-Puppeteer-Educator

Before I started my current multi-part business, I was working one full time job for several years. It was my first office job and it was slightly fulfilling, but involved a cross-city commute and slowly became and more and more taxing. I often worked six days a week and relied heavily on daily naps, but I would still make time to perform a puppet show, play a music gig, or give an art class as often as I could. Read more>>

Lori and Brian Reynolds | Owners of The Grove Mercantile

Since 2005, Lori had always dreamed of having her own brick and mortar store, but a few factors got in the way of pursuing that dream such as needing to put her master’s degree in Psychology to use (after all, that is what she went school for), a pregnancy, a recession, and a few more subsequent pregnancies. Life just got busy and it never seemed like it was a “good time.” Read more>>

Delmar Flournoy | Creative Director, Artist, & Entrepreneur

I’ve always wanted to put a product out that was like putting a piece of me out into the world. Something that I could design on my own, every single detail and bring to life has always been a dream of mine. I’ve been blessed enough to have been able to do that in different ways, not only with my art and product line through Flournoy Studios but also with flipping houses. Read more>>

Elijah Aka Prophetboy | Vocalist & Fitness Coach

I come from a family of entrepreneurs, I am a creative person who knows a lot of people so it just felt right. I was definitely motivated to start my business from my mother. She gave me a lot of confidence and helped me with the logistics aspect of starting a business which really helped me focus on the creative side of things. Read more>>

Michelle Cozzaglio | Co-Owner & Curator

My husband Tony and I created the Oddities & Curiosities Expo in early 2017. We wanted to provide a place for odd artists and small businesses to thrive. A place where its 100% normal to sell bone art, odd jewelry, creepy clothing, spooky art, unusual rare antiquities, taxidermy and much more. A place where anyone can come and be themselves unapologetically and be surrounded by a community of like-minded people. Read more>>

Caitlin Higgason | Photographer at Cait Photo

Coming from working as a graphic designer at a corporate firm, it definitely wasn’t an easy choice to let go of the steady stream of income and begin my journey as a wedding photographer— but I’m so glad I did! A few weeks before I quit that job in 2018 I went to a wedding photography workshop, where the amazingly talented Anni Graham was one of the speakers. Read more>>

Kilian McMann | Illustrator & Graphic Designer

When I decided to start my own business, I hoped to find creative fulfilment that I wasn’t getting out of my day job at a local print shop. When I got burned out after working there for a couple years right out of college, I decided to quit without any other jobs lined up. I had one freelance client at the time, but it was by no means anything I could afford to live on, so I was hard pressed to make this freelance thing work. Read more>>

Nechelle Kennedy | Entrepreneur and Life Speaker

I believe in ownership and sometimes say I’m unemployable, lol. I enjoy the freedom of setting my own schedule to my life and not having a cap of the potential financial growth I can have. Read more>>

Kaitlin Johnstone | Co-Founder Kind Cotton

Kailtin and Kevin Johnstone are partners in life and business. As children, our fondest memories revolve around stories. Kaitlin’s mom & dad would tuck her in, give her a kiss goodnight, & share the adventures of Goofy, Donald, & Mickey. The Disney collection was her favorite. Kevin remembers insisting that his mom read the same baseball book to him every night, religiously. Read more>>

Kim Miller | Owner/operator of tour business

Add some extra activities to our little town. We are at the entrance of Yosemite National Park. Read more>>

Midas B.K.S Productions | Multi-Media Production Company & Collective.

Our thought process behind starting our business was to create more creative opportunities for us and others in Boston. Read more>>

Tracie Smith-Hughes | Photographer

My process wasn’t so methodical or thought out, it kind of organically happened. I’ve always been a photographer. I’ve had a camera on my hands on one form or another since I was a child. I started in the photography world as a concert photographer, primarily documenting the punk/ska and hardcore scene on the east coast back in the mid to late 90’s. Read more>>

JR Rollins | Relationship Manager

Thought Process seems like a formal, educated and organized term. We started our business due to a missing component in our town, a disconnect so to say. The bicycle community is that, a Community. We saw the need for a hub for adventure, inclusiveness, support, camaraderie and we like to refer to our bike shop as a Communal Hub”. Read more>>

Matt Pittroff | Director & Working Stiff Films Production Company Founder

Ignorance was bliss, and in some ways still is. I am not a business person. I am a filmmaker who happens to own a business. I started my first company by default. I knew I wanted to use film as a storytelling medium, I knew no one would hire me without a reel, and I knew I needed a furnace to fuel the fire. The furnace being the business. (I enjoy random nonsensical metaphors.) Read more>>

Teria Brown | Baker and Custom Cake Decorator

Well First it was Iteaching my children that you don’t have to settle, you don’t have to settle for a job from a corporate office, you don’t have to settle for love you don’t have to settle in life. I honestly was settling for the picket white fence life and truly believe that me being a mommy and a wife I couldn’t reach for my goals as a matter of fact for some reason that right there became my goal just to be a mommy and a wife. Read more>>

Yelena V. Krivosheyeva | Director, Producer

Growing up in Russia, I have been passionate about social issues and storytelling since I was very young. At seven years old I watched the Soviet Union crumble in front of my eyes leaving thousands of people, my family included, in a state of deep suffering. That experience sparked a curiosity and the need to help people that continued to this day. Read more>>

Abenezer Mengesha | Multidisciplinary Designer

As I developed and grew in my professional as well as spiritual journey I began to assess what makes me happy and fulfilled, that’s when I was able to start seeing what Abojel really looked like. Growing up in Ethiopia the one thing that I was extremely excited about every year was my birthday party and most importantly my new wardrobe for the new school year. Read more>>

Nika Williams, MBA, MS | Photographer & Enthusiast

So it’s funny… because my photography business is the 4th business I’ve had. I honestly wasn’t passionate about the others… I was ultimately trying to establish supplemental income. However, I have ALWAYS loved photography… ever since I was a small child. So when I decided to pursue photography, it was bigger than making money. I love meeting and interacting with people…Read more>>

Aisha Black | Entrepreneur & Mental Health Rehab Specialist

My thought process behind starting my own business is utilizing my creative skills in a effective way. I am a all-around Creator. Read more>>

Sam Reid | Creative Director of SELFbysamreid jewelry, model and bartender

I honestly never thought about it until I moved to LA and needed a little extra money. One of my friends saw a necklace I was wearing when we were out and was like, “omg I want one of those, are you selling them?” and that was the initial spark in my mind, making me realize that I could really do this. Read more>>

Chelsea Jones | Lash Artist & Hommegirl To All

I come from a family on entrepreneurs, so its always been a goal of mine to have something of my own. When I started Hommegirl, my main goal was to help other women feel beautiful. I’m a mom to toddler and I also work full time so its really hard for me to make time for self care. Read more>>

Justin Gilbert | Social Media Manager

My decision to launch my own business came about very organically. Due to COVID, I lost my job, which left me with a lot more free time. I began creating Tiktok videos of my father’s sports card collection as nothing more than a hobby. People continued to tell me how much they enjoy watching the videos I post as the account began to pick up followers. Read more>>

Jennifer Sherwood | Life Coach

I’m kind of an accidental entrepreneur. I liked the predictability of a paycheck. But, prior to launching my business, I felt burnt out and stuck in my career. Managing work, home, and two small children didn’t leave much time for fun or for me. Read more>>

John Park | Taekwondo Grandmaster

I had to take over the family business. It was going to close. My father started his 1st studio in America in 1971. In the late 1980’s he gave his 3 studios to his senior students. They were all Fighting Champions who were on the US National team. Unfortunately, that doesn’t mean you know how to run a Martial Arts business. Read more>>

Caitlin Wilbert | Filmmaker

I’ve always been very independent. In 18 years as a professional filmmaker, I’ve only been a full time employee for 3 of those years. I like to wear a lot of hats. I like to learn new skills. It’s hard to do that when you are with one agency or company. I’ve worked on so many different types of projects and for so many different clients. Read more>>

Chad Buffett | Prop maker, film producer and special effects artist

After years of working at corporate jobs with long hours, internal product conflicts and multiple fires to put out I realized I was good at what I did but I wasn’t getting the satisfaction equaling the level of work I was putting in. Read more>>

Raysean3x | Content Creator

Originally, I started creating content to escape from all of the negativity going on during the shutdowns and pandemic. While escaping from my own situation, I found out that my content became other people’s escape as well. So I doubled down and kept going consistently. Read more>>

Melissa Bentivoglio | Pilates Expert, CEO & Founder of Frame Fitness

For most of my life I was immersed in the world of elite classical ballet and competitive dance. I found Pilates while I was healing from a broken pelvic-bone injury and the practice was suggested to me as a form of rehabilitation. I loved it, and soon started teaching in Toronto. Read more>>

P. Blake Renda | Co-Founder and Chief Strategy Officer, Dragon Horse Agency

I am a native Los Angeleno born in St. John’s Hospital in Santa Monica, CA, raised in West L.A., grew up surfing south of the pier and playing volleyball with my friends, and graduated from The University of Southern California. I now split my time between Los Angeles, CA, and Naples, FL. Read more>>

Alex Falzon | Sales and Leadership Trainer & Coach

I get most of my energy from meeting people and since finishing university back in 2003, I have always worked in sales. During these years, I always looked for opportunities out there to help me grow and found very few training specifically for salespeople. Read more>>