"Failing is just proof that you tried and you're actively learning."
Jessie DaSilva, dubbed “The Millennial Money Witch” by Forbes, is a coach for ambitious, high-earning CEOs and those on their way to becoming one of them. She combines business and marketing strategy with her intuitive skills to help entrepreneurs connect with their wealthiest, most abundant lives.
Jessie’s coaching is based on the three principles of magic, which are the basic building blocks of changing your life. It’s a three-point formula of aligning intentions, embodying them deeply, and taking inspired action daily. She inspires business leaders to use their intuition to think bigger and more creatively than ever before.
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Table of Contents
Let’s start with a brief introduction first. Introduce yourself to our readers.
Jessie DaSilva: Would you like to learn how you can hack your brain to bring more money, clients, and satisfaction into your life and business? Well, rest assured! The Millennial Money Witch is here to help. I’m Jessie DaSilva and I teach people how to change their lives using mindset methods and practical business strategies and life management tools. The effect of that combo? Magic!
Our audience is interested to know about how you got started in the first place. Did you always want to become a CEO or was it something you were led to? Our readers would love to know your story!
Jessie DaSilva: I never had ambitions to become an entrepreneur until my fourth job out of law school. By then, I had been a private attorney, a government attorney, a legal reporter, and finally worked on staff at a nonprofit. And none of them had been compelling enough to stick with long-term.
Around that time, I had been experimenting with coaching others as a part of building an accountability network for my love of healthy eating and exercise. But I soon realized that seemed to coach people on everything EXCEPT their health!
It was a year into my nonprofit job that I started coaching people on a pro-bono basis to make sure I liked it. And when I realized how much it lit me up to help people solve their challenges and face their fears, I couldn’t believe it. I immediately started making strides to build a business and hire a coach to help me set everything up. When I was fired from my job a week after investing in my coach, I took it as a sign to see it through. Eight months later, I made $30,000 in monthly sales and the rest is history!
“Selfmade” is a myth. We all received help, no doubt you love to show appreciation to those who supported you when the going got tough, who has been your most important professional inspiration?
Jessie DaSilva: Honestly, it’s been all the entrepreneurial women I’ve made friends with and that includes my clients. I’m not as inspired by big-name millionaire coaches and entrepreneurs. I’m more inspired by the women like me who dare to keep showing up, no matter what obstacles they might face. Seeing other people choosing to continue is what always gets me motivated, too.
How did your journey lead you to become a CEO? What difficulties did you face along the way and what did you learn from them?
Jessie DaSilva: I like to say that I became a good coach because I made every mistake in the books. That includes my career before I started my own business and the mistakes I made once I was a business owner. My career was always plagued by the idea that I had to go after the safest path available, guaranteed to get me a stable income. But after almost 10 years of pursuing safety and not seeing much benefit, I knew it was time to take a risk.
Thankfully, I was fired from my job. I’m not sure I would have been brave enough to leave that safety net to go all-in on my dreams. It took a lot of quick learning. I ran out of my severance pay, cashed out a 401(k), charged coaches and course to personal credit cards, and YOLO’d my finances and bookkeeping for the first year. Unsurprisingly, I ran out of money quite a few times. But the most important thing was that I never let it stop me.
That relentlessness is what kept me fired up and, I think, helped me get noticed. Just over a year after starting my business, I was featured in Yahoo! Finance and Forbes Women for my work. Since then, people have continued to notice me. Finally, a little over two years into owning my own business, I was diagnosed with ADHD. Suddenly all of the difficulties I had with staying organized, focused, positive, and consistently made sense. Once I started a treatment plan, I saw how so much of the pressure I carried on my shoulders and the anxiety and depression that always felt like it was one bad day away from taking me down completely melt away. Now, I’m the biggest advocate for taking your mental health seriously as an entrepreneur. I thought I was a good worker before. I wasn’t. I feel better on my worst medicated days than I ever felt on my best un-medicated days.
Tell us about your company. What does your business do and what are your responsibilities as a CEO?
Jessie DaSilva: Jessie DaSilva Coaching, LLC, is for ambitious CEOs and those on their way to becoming one of them. I combine business and marketing strategy with my intuition to help entrepreneurs understand how they hold themselves back so they can remove their obstacles and connect with their wealthiest, most abundant lives.
My coaching is based on the three principles of magic, the basic building blocks I used to change my life. They are: align your intentions, embody them deeply, and take inspired action daily. I like to say that I turn people back toward their inner wisdom. I inspire business leaders to use their intuition to think bigger and more creatively than ever before.
What does CEO stand for? Beyond the dictionary definition, how would you define it?
Jessie DaSilva: For me, CEO stands for Courageous, Evolving, and Open-minded. What I love about so many business owners is how willing they are to fail until they get it right (courageous). I love that they’re always looking to become better versions of themselves (evolving). And, finally, I love that they’re so open-minded. It’s not just about welcoming all people, but knowing that they don’t have all the answers and welcoming feedback on how to improve.
When you first became a CEO, how was it different from what you expected? What surprised you?
Jessie DaSilva: What’s most surprised me is not only that I’m still here, but I can see progress toward my big dream. When I started as a coach, I never went into it with smallness. My goal wasn’t just to make money while changing people’s lives. I imagined speaking tours, best-selling books, and becoming the voice of a movement. I’m finally starting to see those dreams realize now that I’ve nailed down my brand and methods. All those early failures left me fearless, so I have no qualms about reaching out to anyone I want to work with, whether that’s a millionaire client or a hotshot literary agent. Nothing scares me anymore because I’ve lost everything so many times that I know I’ll always land on my feet. Meow!
There are many schools of thought as to what a CEO’s core roles and responsibilities are. Based on your experience, what are the main things a CEO should focus on? Explain and please share examples or stories to illustrate your vision.
Jessie DaSilva: Even though I don’t have staff working under my LLC, I truly see my role as a visionary. Yes, I write and create a lot of my content. Yes, I’m often doing basic work alongside my VAs. But at the end of the day, I’m paid not just to help people solve their problems, but to help them dream of a better life and a better world. And if every person I work with learns that they can create the life inside their heads, then I have no doubt whatsoever that I’m changing the world. No matter what my day-to-day duties are or become, I’ll always see my primary responsibility as imagining a world that’s better than we ever could have designed.
Share with us one of the most difficult decisions you had to make for your company that benefited your employees or customers. What made this decision so difficult and what were the positive impacts?
Jessie DaSilva: The hardest decision I made for my company was deciding to be disciplined with my finances. The coaching world is full of people showing off cars, handbags, and other physical markers of success. I was one of those for a while, too. Except I made excuses for my investments because they were in high-ticket coaches and courses, even those I wasn’t entirely sure I would need. Buckling down meant less flash, of course, but I found my way to celebrate big cash and sales months (it’s called the $10k Twerk Out!). I’ve accepted that I would rather grow slowly and responsibly than have inconsistent results due to inconsistent energy output. My goal is stability, and I know in the end it will serve as my foundation for abundance and success.
How would you define success? Does it mean generating a certain amount of wealth, gaining a certain level of popularity, or helping a certain number of people?
Jessie DaSilva: For me, it’s none of those external markers. It’s having total freedom and control over my life. If I can set my hours, work wherever I want, work with WHOMEVER I want, and love my job the entire time, then I would consider myself incredibly successful.
Some leadership skills are innate while others can be learned. What leadership skills do you possess innately and what skills have you cultivated over the years as a CEO?
Jessie DaSilva: I’ve always innately possessed the ability to connect with others. This isn’t just about having intuitive gifts, but I’ve never shied away from being vulnerable, authentic, and honest with others about who I am or the struggles I’ve been through. I’m truly an open book and the more I continue to embrace this radical vulnerability, the more I see my clients and employees open themselves up to me as well.
The skills I’ve cultivated are definitely in the art of consensual sales. I’ve always naturally been a good salesperson, but I found myself accidentally manipulating people into packages or commitments that they couldn’t afford. I had to learn how to discuss money and results while also respecting the boundaries people have when they say they can’t afford something. I no longer believe in talking people through objections. I discuss prices and results upfront and I welcome potential clients saying no if they’re not 100% excited. I’ve even told people not to join based on their lackluster reactions. That policy earned me respect with potential clients and has only resulted in more loyalty in my client base.
How did your role as a CEO help your business overcome challenges caused by the pandemic? Explain with practical examples.
Jessie DaSilva: I started as a job hunt coach. When the pandemic hit, I instinctively knew the job market would be placed on hold for the foreseeable future. At that point, I had been in business for about nine months. My highest profit month clocked in right before at around $3,000. I thought fast and decided to start coaching people with jobs (or newly unemployed folks) on how they could start a business without having to make all the mistakes that I did. Within 30 days of making that decision, I made $30,000 in sales, sold out my one-on-one offers, and was in the process of creating a group program that would net me $12,600 in cash the following month. Since making that transition, I’ve helped more than 40 business owners of all sizes increase their collective revenue to about $1 million.
Do you have any advice for aspiring CEOs and future leaders? What advice would you give a CEO that is just starting on their journey?
Jessie DaSilva: Fail fast. If you’re too afraid to put everything into it, you’ll just delay the inevitable. Failure is necessary before you can truly succeed and see the fruits of your labor. Failing is just proof that you tried and you’re actively learning. If you’re not failing, you’re likely still afraid to try. So, fail fast and fail often.
Thank you for sharing some of your knowledge with our readers! They would also like to know, what is one skill that you’ve always wanted to acquire but never really could?
Jessie DaSilva: Playing guitar! I think my baby hands just aren’t cut out for it.
Before we finish things off, we have one final question for you. If you wrote a book about your life today, what would the title be?
Jessie DaSilva: ‘Fail Fast & Often: The Secret to Success No One Tells You’
Jed Morley, VIP Contributor to ValiantCEO and the host of this interview would like to thank Jessie DaSilva for taking the time to do this interview and share her knowledge and experience with our readers.
If you would like to get in touch with Jessie DaSilva or her company, you can do it through her – Linkedin Page
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