Thinking through whether to start a business – whether to take the risk, whether to go out on your own – isn’t easy. So we asked some entrepreneurs we admire to tell us about how they thought through the process of starting a business.

Christine Chen | Big Sister Life Coach

After working for big and small companies throughout my career, starting my own business was never something I had planned. Quite honestly, it found me on its own. I had gone through a deep depression after the last startup company I had worked at. I didn’t know what my next steps were. I felt all my work experiences had led me to a dead end and no where closer to where I thought I’d be. After really doing a lot of inner work and soul searching, I started from scratch. What was my core intention in life? What were the values that mattered to me that I wanted my work to reflect? What did I want to learn? And the answer was always there, crystal clear. I’ve always wanted to connect deeply with others through vulnerability and to help others feel less alone. That answer brought me to life coaching. In learning the tools to help me grow and shift my mindset in a sustainable way, I knew this was how I could help others. That was 2 years ago. With each step, one foot in front of the other, it has quickly led me on this path of starting my own LLC while managing and growing my own business. What really excites and drives me is the fact that I keep learning so much as both a person and now a small business owner. Read more>>

Sabina Mach | CEO of Fairytale Design – SUGARPLUM FANTASY AND WEAR

My business started out just as a passion. Everything I do happens because I’m thinking about the creative process, and how wonderful and fun it would be to go on this adventure. I’m never thought about the money in anything I did, that was just a bonus. I grew up on Disney movies, so interacting with animals was normal to me. What I’m most known for is interacting with wild animals. from a fox , to bears , to swans, bulls, wolves, owls and many more 🙂 I had these amazing photos on my Instagram @sweetlittlesugarplum and then Covid happened, and everyone had to wear a mask. But from my experience a lot of kids didn’t like the change, thought the masks were ugly and boring (and I thought the same thing. ) I’m a kid at heart. So I decided to create these one of a kind – fairytale masks, so I could wear, and I would bring them to playgrounds for kids and their parents so they could stay safe. All of a sudden there was a huge demand, parents were calling up saying, can you please send more, “our child is finally wearing the mask.” And then the parents themselves loved it, even the dads are having fun now. Read more>>

Griselda Ramirez | Yoga Instructor & Student

I wanted something flexible that would allow me to go back to school. I completed my yoga teacher training years ago, but had not submitted paper work nor had started teaching since my job was great at the moment. Once my job at the time was no longer fulfilling, I decided to put my training into practice and completed the paper work and started teaching yoga. I began teaching as a volunteer for a senior center in the City of North Hollywood and shortly after I was hired as yoga instructor. It is very satisfying as a teacher to see how your students grow in their practice and further their interest in physical and mind fitness. In 2020 I decided to start my own yoga space (online at the moment) to give myself that flexibility to attend classes and still be able to make a living. I am still doing what I love daily and I get to help others reach their goals during their practice. Read more>>

Jaron Mcneil | Author, Inspirational Speaker and Entrepreneur

I wanted to start a business because of the core principles of what it takes to being a successful entrepreneur. That’s been resilent, persistent and faithful! I have positive influences and mentors in my life who inspire me to become one. Read more>>

Robert Mitchell | Astrologer and Alchemical Agent

I started my own business as an Astrologer because it was the thing that I was the most passionate about. I grew up in a culture where Astrology was seen through the lens of newspaper sun sign columns and light, cliched filled books. Over thirty years of my study and work with people I found that Astrology much more resembled quantum physics than it did what most people think of it as. Every single person, whether they believe in Astrology or not, has a chart that communicates the unique structures of their consciousness that creates their perceptions and experiences. This field of experience is present at the moment of their birth and will be a constant presence during their lives. Astrology offers the opportunity to partner with this intelligence and co create with it, rather than assume that one’s reality is static. I didn’t see anyone offering this kind of counseling to people, and despite it not being viewed accurately by the culture at large. Read more>>

Ariella Israel | Visual Artist

My initial thought process was me being able to inspire the younger generations to potentially follow in my footsteps. Growing up and even until this day I have people coming to me as though there’s no future In What I’m pursuing, but I’m going to show them better than I can tell them. There is a future in the Visual Arts field all it takes is you believing in the talents God gave you. Read more>>

Noah Say | Creator of Project Thirtyfive

Would I wear this shirt/ sweatshirt? Why am I wearing it? These are a couple of questions I ask myself when I’m designing a print. A lot of companies and brands just don’t do it for me, and creating my own just felt right. Putting what I love on a shirt or sweater and sharing that and seeing people actually buy it-let’s me know there are others that like what I like and that’s always a great feeling. Being apart of something you love and believe in was a big vision of mine when creating Project Thirtyfive. Read more>>

Sean & Shannon Scott | Founders

It’s an interesting question because Shannon and I both had great careers already. Shannon was VP of Marketing at Asics. I had stints at Nike, Asics, and Vans and was a founding member of TOMS. We had had some great experiences and had learned from some of the best. I won’t lie, we considered just retiring. But we both felt compelled to address some missed opportunities. We had unfinished business. There were three main motivations: – Overseas mass production is a serious problem. Not only is this model outdated, slow and inflexible but also the sustainability and human rights record of fashion mass production is criminal. Overseas mass production is designed to improve costs for companies; not for serving its customers better and certainly not for improving the lives of its workers and community. – Social impact in fashion is often focused on those in need in far away lands. We see plenty of need closer to home. Read more>>

Heather & Leah Stewart & Finkelstein | Composers/Singers/Songwriters

Starting our composing business happened quite naturally. We are both established singer-songwriters and had worked with each other off and on over the years, having met at the Malibu Music Awards back in 2011. This included a U.S. tour together and being in a successful musical comedy act. Leah was writing a theme song for a talk show and asked for my input. We quickly realized how much we trusted each other’s instincts and the flow of creating together. Our creative process was also so much quicker, as we are a constant sounding board for one another. There is such a severe lack of female composers in TV and Film we immediately put the word out that we were a female duo for hire. This led to scoring our first indie feature, writing theme songs for three internet TV shows, a music supervising gig and signing with a music placement company. It became pretty obvious we needed to start an official business at this point. Read more>>

Nissa Prizzi | Vibrancy Wellness Coach

Starting my own business really came from feeling compelled to help others. It began by wanting to use my voice to create community around the struggles of motherhood. Society can paint the picture that motherhood is this glorious magical calling where raising children is all fresh baked muffins and laughter. I wanted other mothers to know that if motherhood was feeling like a big mix of wonderful and really hard, they were not alone. Connecting with others that way then led to wanting to share other things I had learned along the way as I searched for my own health. Now I have the privilege of helping other people move out of confusion, frustration, and paralysis of sickness into vibrant lives filled with energy and hope! It is pure joy for me to watch people experience breakthrough and hope after being so weary and alone in their struggles. I saw that there was a need for more connected and simplified solutions for health. When I didn’t find it, I decided to create the business myself. Read more>>

Kim Mahair | Photographer, Stylist, Designer

I’ve always loved vintage clothing, not only because my style and sensibility seem to align better with past eras, but because with vintage it’s far less likely that you’ll be able to find the same garment anywhere else. There is something off-putting to me about going into a store, picking up a dress or top you love and seeing 10 or more replicas of it hanging there. Last year I was inspired by this sleeveless coat Katharine Hepburn wore in Guess Who’s Coming to Dinner and decided to design something similar with my own spin on it, so I teamed up with a pattern maker and brought it to life. I have a long list of pieces I want to design, but the last year has been an education in the cost, time, and effort that goes into making one design. I was then faced with the dilemma of how to start a clothing business with just one piece. I have a large collection of vintage clothing, so I decided that I would begin selling the pieces I was ready to part with and add my own designs in as they come. Read more>>

Rick Baker | Executive Director, The Becky Baker Foundation

My wife passed away from stage IV breast cancer. One of the last things she said to me was, “I’m just sorry that no will ever remember my name.” I promised her that no one would ever forget her name and launched my breast cancer foundation in her name, with the expressed purpose of saving as many lives as possible by giving away free mammograms to those who cannot afford the screening. Since her passing, I have provided over 2500 free mammograms. I could not save Becky, but in her passing, she has saved hundreds of others from the terrible death of breast cancer. Read more>>

Elizabeth Woolf | Songwriter & Producer

Every artist is tasked with the introspective challenge of finding his or her creative voice, but it was in my senior year of college, that I discovered my voice as a business owner as well. In my final semester at UC Berkeley, I took a course in media strategies and design thinking taught by Diane Dwyer. At the same time, I was producing and directing a self-written musical titled “Dreams of 18” for my senior thesis. Diane’s course material fit like a glove and overlapped seamlessly with my passion for storytelling. I learned that there are two types of stories that are presented when an artist releases a piece of work; the art itself, and the story about the art. These innovative ways of thinking about the artist’s relationship to storytelling changed my viewpoint. I fell in love with the process of owning my story as a woman owned business, and as a songwriter, which requires a different type of confidence than owning my artistry. Read more>>

Keturah King | Journalist | Actress | Entrepreneur | Producer | Philanthropist

I am incredibly passionate about Africa, Africans and Black people (particularly women and girls) within the diaspora. As a result of this, I endeavour to ensure that all I do centres the people and their projects, as opposed to me and my brand. I’m very sure of my place in the world – so I use my creativity and connections to assist those who maynt be as confident or secure. As the erstwhile host of CNN African Voices, I revamped the show and centred it on the young, cultural, trendsetters that were making an impact on the continent and further afield. Through my travels, I have realised that simply sharing stories of what someone has accomplished isn’t enough. Now, I need to inspire the next generation to believe that they can achieve anything they set their heart’s to. When you know where you’ve come from – your path is a lot clearer…even when you’re simply waking in faith. Your ancestors guide you. Ergo, I am building an indigenous animation company to captivate, educate and inspire the hearts and minds of young, Black children worldwide. Read more>>

MomTalk | Music Production House

It happened naturally when we went through a life shift, by becoming mothers. It was a freeing and natural expression that grew into something larger, that we found people were drawn to. It’s really turned motherhood into an empowering influence over our music career. It was important for us to keep our authenticity as artists and bring it into the film/tv/ad world. Keeping our unexpected and off center approach while making something relatable that would elevate other creatives and transport listeners into a different place. And it brings us a ton of joy to make music with each other all the time. Read more>>

Arian Mahboubian | Photographer & Content Developer

I never had imagined my photography career to take off the way it has been in recent times, let alone even thinking I could turn my photography passion into my own business. My first year taking photos was mainly scenic with lots of landscapes from adventuring out into California’s Eastern Sierras; what drove me there was simply to escape the city life and see what nature has to offer. Any chance I got I would take the drive and be in some of the most remote places I have ever been. Little by little I gained attention from family, friends, and colleagues, to the point I was being asked to take family photos and birthdays. Growing up, my direction in life was limited with the lack of inspiration and guidance; photography gave me that inspiration I needed to guide myself into a profession I not only love, but also one that has brought me a sense of purpose I was desperately craving. Read more>>

Mathew Young | Director, Actor & Cinematographer

Before anything else, I was trained as a musician from a very young age. In a nutshell this continued into my later life and I found myself sitting in my home music studio one day thinking to myself “hey, there’s a bunch of my actor friends who required voice demo’s for their portfolios”, and wallah, YoungOneStudio was born. How the business became what it is today, that’s a different story. Both my partner, Tamiah Bantum, and I come from an extensive acting back ground. Having both been on stage since around the age of 12 we made the natural progression into acting in front of a camera several years later. We both got representation in our late teens and began commercial work with the odd narrative tv bit here and there. The narrative side of our performance life stayed mostly stage based as screen roles are harder to find and competition is fierce, especially in Perth where we grew up. Read more>>

Kiara Burns | Fitness Trainer and Movement Coach

I am a classically trained ballet dancer of over 20 years. Movement has always been my life. I graduated in May of 2018 from the Boston Conservatory at Berklee with a BFA in Contemporary Dance Performance with an emphasis in Ballet. It was expected by everyone including myself that I would go straight from there and audition for dance companies, but something told me not to. I had started working at Pure Barre during college because I thought it would be a great way to make money, and I ended up falling madly in love with fitness. I was injured a lot while I was dancing. I was actually injured so much that the night before my last surgery the anesthesiologist called to ask me if I was a professional stunt woman… yikes. I was incredibly knowledgeable and passionate about my body, and I was determined to make it powerful, strong, and full of grace. I graduated, moved out to Los Angeles and immersed myself in group fitness as well as one on one training. Read more>>

Lisa Raphael | Artist and Maker

I’ve always been an artist in some form and I have always loved lighting. I could never really find anything that was cool, that also wasn’t a mortgage payment. I decided I would start making my own creations. I wanted to make money doing the things I love. Read more>>

Cindy Arenas | Wedding Planner & Event Coordinator

I have to be honest here and say I really didn’t have a “thought process”. I was working at The Walt Disney Company when I coordinated my first unofficial wedding. It was for a friend of a friend and I had no idea what I was getting myself into. I was thinking…”Sure, this can be fun! I assist a President, EVP and VP. How hard can this be?” I planned this wedding from start to finish and the day itself was one of the hardest days of my life. My husband asked me. “Is this something you’d want to do full time?” and I thought for a moment and said “Heck yeah!”, My mind went into fantasy mode and I was really seeing a future filled with weddings. I thought of a business name and even asked my coworker to introduce me to her sister who had just gotten engaged. I was ready for my next wedding, and a year later I quit my full time job. I really dived into this career head first without a clue of what I was doing. I gotta say, looking back, I was a little insane for doing that. So, to answer this question, my thought process came as I learned my new career and new industry. Read more>>

Beberly Morales | Real Estate Agent/ Investor

Being a business owner will take a big commitment and endless hours of building. When you are passionate about what you do and are driven to be the best it won’t feel like work. Some tips I would recommend to anyone thinking of starting their own business would be to hire a coach. Learning from others mistakes will save you time, energy, and money. Talk to people who are doing what you want to do. Be willing to volunteer or intern in exchange to see and shadow what it takes to get where you want to be. I quit my 3 jobs right before doing Real Estate full time and took a leap of faith. I saved 3-6 months in advance to cover basic needs and expenses. I partnered up with an experienced real estate agent and took action. One thing you won’t regret is becoming your own boss! Be ready to have a schedule and accountability partners it’s easy to slack of and postpone important task if you don’t have a schedule. Read more>>

Soni Mizrahi | Architect & Filmmaker.

I´m an Architect / Filmmaker. This might sound crazy and most people ask me the same two questions: What do they have in common? And, Do you work full time in both? The answers are: more than you think and yes. To fully understand what I do, first and foremost you have to understand my background. I grew up in Mexico City and from an early age I noticed that I had a certain interest for the arts. Before I could even talk, my parents told me that every time we went to a toy store, I ended up picking a drawing book and some crayons. As I grew older, I developed a fascination for storytelling. Every time I went out to a crowded place, I caught myself staring at people and developing an ingenious backstory. When the time came to make a decision regarding what I wanted to study in college, I decided that Architecture was a better choice since the program covered more art subjects. Read more>>

Lauren Alexander | Wellness Apothecary Owner/Entrepreneur

I wanted to start my own business to be able to share my creations with the community and help people through plants and wellness. It’s a great feeling to be doing something that I truly love and have a passion for, while connecting with people and learning more about their lives as well. I learn something new each day, whether its by my own research or speaking to customers and amazing people along the way. Read more>>

Mara Freedman | Social Media Stratagist & Founder

My decision to start my own business came from a lot of different reasons that can all probably be boiled down to happiness. I was working at Sony Pictures Entertainment, in the Theatrical Marketing division for the most kind and generous boss, where the idea to do something on my own first started. While there, I was doing a job that did not quite exist on paper, and my boss, Jamie Kramer, gave me the push to leave. She encouraged me to go out on my own, knowing that I had the creativity and skills in me that I didn’t know I had yet. It took me a little while to get to that point as a searched for the right opportunity, all while slowly taking on clients. Shortly thereafter I took a short lived creative director role at a company that I truly disagreed with the ethos and whose client roster was nothing that I would really want to associate myself with. I became seriously ill, and after a week in the hospital, I planned my exit, deciding I was finally ready to go out on my own. Read more>>

Fernando Reyes | Visual Artist

I needed a change in career. After a 17 year career with Bank of America from branch banking operations to software development to my last positions as operations management for the banks bankruptcy accounts nationwide – I had enough. I prepared for my departure a year in advance and managed to leave debt free with money in the bank to start a new career in the arts. Having management experience was a real plus as i structured my day understanding that I needed to be productive and disciplined. Considering I was in my late 30’s I felt that I was still young enough to pursue the career I always dreamt of. I had an enormous learning curve to overcome but my perseverance was enough to see me through my trial and errors. I immediately enrolled at San Francisco City Collage and took as many art classes as possible. Eventually in 1993, I moved to Chicago with my partner Daniel (now husband) and applied to The School of the Art Institute of Chicago. Read more>>

Julie Pinzur | Founder & Creative Director of Mokuyobi

I was always interested in the construction of sewn goods from a young age. I would take clothing and bags and deconstruct them to see how they were put together so I could then create my own versions. Upon doing this [unbeknownst to me at the time] research I came to realize that most items, especially bags are cheaply and poorly made. I didn’t understand how a brand could make a decision to produce a worse product with inferior materials and construction techniques on purpose and disperse it into the world without a heavy conscience. Growing up I was always very expressive, especially through my clothing. My experience was that wearing bright, fun colors not only let me voice my inner sensibilities and personality but it also heightened the mood of myself and others around me. I feel very strongly that color has a positive impact on our disposition as well as the filter we see the world though. Read more>>

Julius Gordon | Songwriter & Vocal Coach

When I had first moved to Los Angeles I did a lot of singing gigs around town. When I would go to a lot of the dress rehearsals it would take me know time to go through everything with the band because I had the language to communicate clearly what I needed to the musicians while the other musicians would struggle a bit. So I decided that I would provide a service where musicians can come and not only to learn how to be more proficient performers, but also come and acquire the knowledge to be able to navigate and thrive in professional settings. Read more>>

Filippe Baruc | Tattoo Artist and Businessman

It wasn’t easy. I worked from 13 to 21 years old, but always with the dream of being my own boss and having the freedom to test my own ideas. I am from a humble family and without any knowledge of business, and whenever I said I was going to have my own business they laughed and made fun of it as if it were just a dream and that I could not get. I think the biggest motivation was to show that yes I can and if I can anyone with willpower, focus and determination can. Read more>>

Christopher Mercier | President & Founder of (Fer) Studio, Practicing Architect & Visual Artist

I officially started (fer) studio back in the summer of 2002 but in reality I started it probably a number of years prior in my mind and actions. For me starting this business was part of a longer trek that I started as a young adult and maybe even sooner as I always imagined I wanted to some way find a very personal way to contribute to the world, one close to my heart. Read more>>

Yinka Freeman | Owner, Triple Pocket Events

Starting my own event planning business had been in the back of my mind for years, but like so many others out there, fear always took over. People around me would always tell me to start my own business and that I would succeed but it was hard to fully listen. After many conversations with the people around me that I trust, I finally made the decision to take the leap of working for myself. Before making the final decision, I sat with myself, reflected on my past roles and really thought about the knowledge I had gained that would support my journey into entrepreneurship. With over 15 years of national and international industry experience, I was confident in my skill set and knew that I would have a strong network to support me. I wanted to build a company that aligned with my personal values and before coming up with a business name, I came up with the core values for my company and have been building Triple Pocket Events based on those values. Read more>>

Lyle Michaud | Pianist, Instructor, Composer

I’ve been around people who have been entrepreneurially-minded. My dad started his own industrial cleaning business, my older brother launched a web and graphic design company, and several uncles of mine also started their own businesses. I even remember as a kid learning the story of my great grandmother who opened her own little convenience store out of her home during WWII. So in my teen years, as I began to think more about what my career would be, it felt natural to consider starting my own business. And I figured, I’d might as well make money doing something I love! I’ve been playing piano since the age of five, so a music career seemed both obvious and desirable. Since I had begun to establish a reputation for being a serious and passionate pianist and performer, and since I had devoted most of my life to studying music, people began asking me to teach piano to their kids. I was still in high school at the time, but I figured why not! I quickly developed and discovered a passion for education and sharing my joy of music with others. Read more>>

Kissa Starr | Cultural Event Producer/Entrepreneur

Prior to me launching Plants and Teas, I was producing a Comedy Show at Hot and Cool Cafe in Leimert Park. March was our last show due to COVID -19 and I was inspired to do something for the community that would help heal and bring more happiness into the home. Plants always made me feel good and teas are soothing and healing. I was thinking, what can I do that would help the community during these times? I thought of all the things I wanted to provide to my community like Plants, Sea Moss, Sage, Palo Santo, Teas, Eucalyptus, etc….and I wanted to have them all in one place and that’s how Plants and Teas was born. In July, we launch our store in a store concept at Hot and Cool Cafe and was able to provide an array of products to keep our community home and health vibrant and flourishing. Read more>>

Diana Sabb | Event Producer & Designer

My mom started her own business as a hairstylist when she was younger and my dad owned his own business as well. This promoted me to want to start my own business. I knew I didn’t know everything about starting a business so I utilized people I knew, got a mentor and some one who had been in the industry for a long time to really help me navigate. Prior to starting my business I had an internship that really allowed me to be apart of all different types of events. This helped when it came to finding out what type of events I wanted to do. From there I was like ” I can do this” and then there was the entrepreneur mindset of long nights, networking, styled shoots, finding what I wanted my brand to be and working with so many incredible vendors that have been in the industry longer. I have learned so much. Once I found what my flow would be it became easier. Read more>>

Mugzy McFLY | Creative & Fashion Designer

How am I gonna find this need to create. I dug deep, researched. Made every mistake & decided there were no plans bs. Read more>>

Ari Jogiel | Fashion Designer

I started to receive a lot of interest from brands across the States to help them with consulting, development, and manufacturing and saw that I could help them and many more, so decided to start a new company that specialized in this. Read more>>

Jefel Jadoo | Fashion Designer & Entrepreneur

Growing up at my younger ages it was quite strange how I was not quite into dressing up how you would hear maybe other fashion designers how they were dressing up. But as I started getting older, I was developing this passion for clothing, accessories and just overall fashion. I have tried multiple other career in different industries, but nothing seems to make me have this awe like fashion. When I first started my business the plan was to start with clothing, but then I thought about going a different route that could be more affordable which lead me to jewelry. I decided to walk into designer stores such as Louis Vuitton, Gucci, and a few more names to see their fashion jewelry. After taking a long look at what they have, yes they may have high quality pieces, with good designs, but they are not perfect and the best. That’s when I decided I would start here, with fashion jewelry knowing that I can do the same thing even better. Designing and creating my own jewelry pieces, and basically doing everything my own way. Read more>>

Christie Carlin | Laser Tattoo Removal Specialist & Tattoo Lover

For the first twenty years of my career I worked in the service industry, but I dreamed of one day owning my own music venue. While I learned and experienced a lot of personal growth, I decided to focus on something new and I went to school for nutrition. Which led me to working in sales and marketing for natural and organic foods. When I later needed to make a shift in my career due to health reasons, I followed a passion of mine and enrolled at Rocky Mountain Laser College. Within a year I had already found a job within the industry. I helped the owner grow the company into three locations while doing the vast majority of the treatments. This situation did not end the way that I would have preferred, but I gained a large amount of experience from my time with the company. I was passionate and possessed the credentials but found finding another job was impossible. I decided that I needed to take control of my own destiny and I started writing a business plan. Read more>>

Angel Amor-Smart | Esthetician & Baker

Baking has always been an outlet for me. I bake just for fun, to relieve stress, or just because. I’d always wanted to have my own bakery or restaurant but never seriously acted on it until 2018. Read more>>

Gifty Boakye | Modelprenuer , Public Speaker & Host. Current Graduate School Student

I started modeling when I was just 16 years old so at that age I was not only impressionable I was hungry for success , which at the the time meant money, game, buying my mom a house, you know that kind of thing. Soon after I moved to Nyc still in my teens and going in and out of agency go sees, casting calls I quickly noticed how under represented black women, dark skin women, African women were in the fashion industry. One thing about me I’ve always been proud of my features, took me some time to grow into my skin ( imagine that) but my Ghanaian roots have always inspired me to stand out. Later in my career I went in for a NYFW casting for , Michael Costello, I was told my was was amazing but I’m a bit too curvy . I was a 4/6. It hit me then that there should be a market. Read more>