One of the most under-the-radar benefits of entrepreneurship is its ability to build fortitude and make the entrepreneur a more formidable person. Challenges – particularly the crazy, unexpected ones that take on a life of their own – build character and confidence. And the unexpected surprises to the upside, the crazy good moments offer a high that’s hard to reproduce elsewhere. The charm and the challenge of entrepreneurship is dealing with the crazy things that happen and so we’ve asked some fantastic business owners and leaders to share some of their stories with us below.

Aruna Inalsingh

I once was referred to a client, who successfully sold his previous company and was starting a new one. He needed marketing help and, when I met him, I was impressed because he knew exactly what he wanted. My first assignment was to survey existing and prospective clients. I learned that they wanted to consume regular content from us. In agreement with the client, I developed a content calendar for PR, newsletters, blogs, and social media, and I wrote and distributed those communications. Once that program was on auto-pilot, though, the client shared that I didn’t give him what he expected. What he really wanted was an integrated marketing plan to generate leads. So, in addition to the messaging and thought leadership content that was scheduled, I enhanced those communications with campaigns to generate and nurture new business. Turns out, though, the client wasn’t pleased with that either. What the client actually wanted was sales collateral. You guessed it, after the collateral was produced, I still wasn’t satisfying the client. At that point, we were at our 2 month mark, and our meetings were becoming more contentious. Thank goodness I was being paid, but I realized that this was not a healthy professional relationship for me. After sleeping on the situation, I “put on my big girl pants”, and asked the client if he might be able to find someone else who was better suited to the role. Initially, he was appalled but, after he thought about it, we agreed to end my contract. It was the first time I “fired a customer”, and it certainly wasn’t easy. It was worth it, though, both the client and I ended up in a better place. That lesson has been carried with me ever since. Read more>>

Piper Watson

Life had been pretty crazy for me leading up to March of 2020. In 2018 I left the nonprofit makerspace that I co-founded, feeling lost, burned out, and totally confused as to what to do next. So I vanlifed for 2 years and 8 countries, with 2 not small dogs, to try and find my answers. What I found was that people continuously coming to me for business and life advice since I had successfully been running multiple creative businesses for 10 years. So in February of 2020, my husband and I settled in a new city and I officially launched as a life and business coach. I quickly secured a six-month contract worth half a year’s salary to coach an entire leadership team for a community acupuncture franchise. Then, the world stopped. One month into our coaching engagement, the CEO called me in tears that because of the pandemic, they would have to close the doors to all three of their locations indefinitely. She was understandably terrified and heartbroken at having to lay off her entire team of 40+ people, and just like that my entire revenue stream disappeared. Which, surprisingly, wasn’t the primary thought. My initial reaction was that I knew I could help her. I had spent an entire year training as a coach to help entrepreneurs be able to manage their mind and their emotions along the roller coaster of running a business. So I told her to just continue with me one-on-one, totally for free, for one month so that she could at least have some unbiased support to help her figure out what’s next. It wasn’t easy. My own financial worries needed to be dealt with as we had incurred moving costs, were still trying to get settled and now both my husband and I were out of work. So we both just did what needed to be done, we swallowed our pride around our experience and higher education degrees and he got a job packing boxes at Amazon and I got a job stocking shelves at Trader Joe’s. Even with that, it still felt like the right thing to do to offer my client free coaching in a whirlwind of global chaos, grief, and uncertainty. So she and I got to work in my off hours at Trader Joe’s. I helped her feel all the feelings and brainstorm all of the possibilities. Two weeks in we had come up with a way to completely reinvent her business using some of the culture and ethos that I was surprised to learn at Trader Joe’s so that her business could operate more streamlined, cost less, and be more FUN for everyone involved. So when she received a large and unexpected grant to open back up in May of that year, she brought me on as a full-time coach for her and her staff to help everyone transition into this new business model and collaboratively create a healthier work culture that all were inspired to participate in. The pay was nearly double our original contract so needless to say, I didn’t stay at Trader Joe’s for too much longer after that. But it just goes to show that when you that in any business, when you show up in service and focus on delivering value to people, the money always comes and things always get figured out. Read more>>

Stephanie Pantoja

Well the craziest story is how I really got started, I was reached out by the CEO of Solin which is where I now run my programs and fitness challenges. I basically was “bullied” into launching a fitness challenge by Matt (Solin CEO) lol. He had emailed me a few times and I ended up scheduling a call with him and every time he would call I would be “busy” I remember I was doing cold calling software sales and while I was at work one day Matt had called again lol. I said “Could you please call me back at another time, I am busy at work”. Then he hits me with the “Are you sure you want me to call you back or are you just trying to get me off the line” (he said something like that I can’t fully remember) he then said “Steph I have an opportunity for you to make $$$ without you putting any money up how does that sound” Then I said I most defiantly want you to call me back and gave him a time that same day. As soon as I got off of work he called me again and finally we spoke and he explained to me what Solin was and how I had so much potential to create a business selling programs and challenges based off of my content on my social media. I had been documenting my weight loss journey on TikTok for about 7 months then. I was very apprehensive in launching any type of program or fitness challenge because I had not gotten to my goal physique yet and I feared the judgement of others since I don’t have the “ideal fit body”. Also, I never intended on training others or getting into the online coaching space. I was on that call with Matt for probably almost an hour and he convinced me that I had what it took to create a successful challenge. So I took the leap of faith and launched my 21 day Reset challenge and made my monthly salary at my 9-5 in about a week. I ended up going on a “medical leave” from my job and never looked back since. I was able to sustain myself by selling that 1 program, it truly woke up the entrepreneur in me. Since then I have launched a weightlifting program and recently another challenge. I also am launching a 1 on 1 online coaching business in the next several weeks and I am beyond proud of myself but sometimes I do have imposter syndrome. I am in disbelief that this is my life, like I am really an entrepreneur. My life has dramatically changed in the matter of 1 year. I’ve always prayed “God I just to want to serve my purpose in this world”. Ask and you shall receive, I am very excited for what the future holds with my new career. Read more>>

Barth White

I grew up in Las Vegas and spent my teenage years working for the casinos. I never got a formal college education as I attempted to start a heavy machinery business out of high school before eventually working jobs at the casinos. After the Aladdin hotel was raided in 1980 by the FBI the casino was shut down and restricted the amount of money bellmen could make dropped significantly. I had a friend in California who was a wallpaper hanger. I visited him and thought it looked like something I could do. I returned to Vegas and decided I would be a wallpaper hanger. I began walking the street advertising. This was at the time Howard Hughes died. While looking for his will they had tore into the walls of his bungalows. I was hired to fill in and repair the holes. After three days I still hadn’t filled the first hole. I then hired some professional paper hangers. They got more work done in three minutes then I finished in three days so I began to apprentice under my employees. I slowly learned the craft and this is how I got into painting. I began to apprentice under painters I employed. Some of the casinos began hiring decorative artisans so I decided I needed to learn decorative painting. I had a natural gift for seeing colors and patterns and excelled in decorative painting until I became the top decorative painter on the strip. I was Steve Wynn’s personal artisan and to this day have artwork in almost every casino on the strip. Read more>>

Dan Davis

When I started Stiry (stands for ‘Stories that Stir”) in 2016 after following some direct inspiration, with no money and no clear vision, I had no idea by business would save my life. Literally. As I was busy producing documentary stories on the most inspirational stories around the world, I was battling multiple unknown chronic illnesses for over 20 years. In 2019, I had a blood clot in my leg that wouldn’t go away. It just so happened that at that time I felt inspired to produce and direct a documentary on a woman named Kim White. Kim was battling a one in a million cancer diagnosis and we both felt inspired to do a feature length documentary on her journey. We had no funding and no real plan, but we jumped. The craziest thing I did was begin production on such a large scale film without any funding, but I personally funded the project with debt in hopes that we would raise the money along the way. I realized that while the film was meant to capture her legacy and help many people in their own battles, one of the main reasons I felt inspired to tell her story is that she would ultimately save my own life. Little did I know that at the time we were filming I had a problem with my kidney where blood was not flowing well back to my heart when I would sit and stand. During that time Kim’s health was failing and she unfortunately passed away in the middle of the production. On my last visit to her in the hospital, she asked me to pull up a chair and “tell me what’s really going on with your health.” She knew. She knew something serious was going on. And then she made me a promise right before she passed, “I’m going to figure you out.” I didn’t think much of the promise until we interviewed her interventional radiologist for the documentary. During a break in the interview I said, “You should try to figure me out. I’m kind of a medical mystery.” I told her my symptoms and she said I likely had several syndromes that she happened to test for. One in particular that had to do with my kidney. That night following our interview with her, Kim’s interventional radiologist looked at my charts and scans and found the problem with my kidney. She subsequently got me into the only specialist in the state who knew these conditions inside and out and within the next two years I was diagnosed with every syndrome she named that day of her interview and had two life preserving surgeries just months later. One of which restored blood flow to my heart and allowed me to sit and stand again after 18 months of lying flat almost full time. Read more>>

Mario Acevedo

My journey as a writer began in college. I received a D in sophomore English and was told that I wouldn’t be allowed to graduate unless I passed another English course. Since I needed only one credit hour, I was offered either business writing or technical report writing. Being an engineering student, I chose the latter. The first day in class, the professor handed out pamphlets for us to critique to show that just because something was in print didn’t mean it was written well. He then said one of the most profound things I’ve heard in my life: “The purpose of writing is to communicate ideas as clearly and concisely as possible.” It was like a light went off in my head. Until then, I thought the point of writing was to sound smart. When I graduated I was commissioned in the US Army and there, sought every opportunity to write. Since every writer should be an avid reader, I spent hours in the library and one day had the most dangerous thought that could infect a wanna be writer. After reading a particular book, I thought, if this guy got published, so can I. Seventeen years and six trunk novels later, my debut novel was published so you can say that I’m a slow learner. Along the way, I found myself divorced and unemployed and to avoid being homeless, lived in the basement of an ex-girlfriend’s house where I wrote that novel. The idea for that novel arose after my previous manuscript failed so spectacularly at getting the attention of an agent or NY editor that my queries didn’t even receive rejection letters. I was so dejected that I decided to write the most ridiculous story that came to mind, of a detective-vampire investigating an outbreak of nymphomania at a nuclear weapons plant, which was published as The Nymphos of Rocky Flats (HarperCollins 2004). Read more>>

 Michael Richey

Most of the things you experience while investigating the paranormal are personal. Feeling the hairs on your arm stand up, a sudden cold chill, or seeing shadows from the corners of your eyes. Having a collective experience where two or more people experience the same thing outside of their own bodies is a rare event. I’ve experienced a few of these events in a collective setting, but nothing has come close to the one I had with a group of twelve strangers at the Indiana State Sanatorium located in Rockville, IN. Read more>>

Cody Scott

I’ve always wanted to travel the world, never would I have imagined I would see more than 47 states and 3 countries in 5 years of opening up a business. My work has captured the attention of some of the biggest players in the game. I have had the privilege to partner with these companies in creating documentaries about their work and the stories that come out of the process. This has landed me in Canada, Italy and over 47 states in America. The part is see to be the most interesting is that I am able to do this with just a camera, a lens and a microphone. A few small tools take me across the world. As I travel I get to serve the kingdom, blessing people I encounter with gifts, money, food, prayer, comfort and attention. Read more>>

Lauren Sanders

I wouldn’t necessarily say these are crazy stories or unlikely to occur, however I have been blessed with the opportunity to work with several well known names including reality TV stars, well known athletes, multi-millionaires, famous start-up founders, and children of mega stars we all know and love. Receiving the trust of these individuals warmed my heart, and I thoroughly loved working with each of them. Read more>>

SJ Janjua

A huge part of what I do with my business, Empowered for Equity Consulting, is helping give others the tools to create more inclusive environments. I was inspired to make this part of my mission because I have had many experiences where I have been othered or excluded because of the different identities I hold. We spend so much of our lives at school, at work, and in social environments, why not make these spaces as inclusive as we can?! Read more>>

Nitya Jain

The world of photography is very intriguing and colorful but still very underrepresented by women and people of color. I do think that clients and decision-makers are hesitant to try new talent or women of color. Having been in the creative industry for almost 20 years with a career spanning from architecture, and visual design to photography, it has always been that extra mile, and a higher standard that I have needed to showcase as a woman of color. Things are moving in a positive direction where more organizations, and collectives support and promote creatives who are otherwise overlooked and not well-versed in the industry vocabulary. Read more>>

Katherine Bailey

When I initially branched out on my own from to launch Gemini Consulting, the company where I was previously employed hardly even had a handful of minority consultants, and only one other black woman within that handful. Honestly. in my field the large majority of consultants are Caucasian men, followed by Caucasian women, who are all generally much older than myself. I bring inclusivity to my field being a young woman of color, having that option for my clients has been very impactful to my business as well as to the experience that my clients get from their workshop with Gemini Consulting. Being able to have a woman lead workshop and/or being able to have a workshop led by someone younger in this climate makes the workshops more relatable often times, which results in high engagement. Read more>>