The Million Dollar Pivot: Sam Vander Wielen's Playbook For Online Entrepreneurs

Forbes

10-05-2025

Sam Vander Wielen
When I Start My Business I'll Be Happy: A Practical, No-BS Guide to Successful Online Entrepreneurship turned one week old when I sat down with the author, Sam Vander Wielen. She was in the midst of a whirlwind of launch activities, which was evident in her voice—excited yet reflective.
She just returned from her walk on a crisp New York City morning with Hudson, her beloved Bernadoodle.
Her eyes brightened at the mention of her furry friend. 'He's been everything to me through all of this,' she said.
Sam's career path from corporate attorney to online entrepreneur was anything but linear. The lack of fulfillment as an attorney came to a crossroads when she decided to double down on her health coaching side hustle. The pivot to her legal templates business (what she's widely known for now) emerged unexpectedly when she was attending a wellness festival to promote her health coaching services.
Suddenly, she ended up with a line of entrepreneurs seeking legal advice for their businesses and her lightbulb moment became evident.
"Sometimes your failures teach you more than your successes," she reflected. 'I was passionate about health coaching, but it wasn't a good business idea. My legal templates business was a great idea for a product. There was a lot of demand and not much supply. I also knew how to differentiate it.'
Sam's business advice is contradictory from the marketing gurus claiming to follow your passion and guaranteeing overnight success. Centered on the book's title, the then-when approach to happiness rarely (if ever) pans out. Rather, as she states, happiness doesn't come from business success, but rather from how you approach life regardless of external circumstances.
'If you attach your happiness to external factors, you'll never be happy. It's just a carrot that keeps moving. Once you have a million-dollar business, you're surrounded by people with $5 million businesses and once again – you feel like you're not good enough.'
When I Start My Business, I'll Be Happy: A Practical, No-BS Guide to Successful Online ... More Entrepreneurship
I think what makes Sam's words connect deeply with readers is her vulnerability. She opens up about tragically losing both of her parents in a short time. Through these profound losses, Hudson became her emotional anchor.
Sam's parents influenced her entrepreneurial spirit as they led by example. Her mother, a professional figure skater turned physician, made the career pivot at 41 – showing her that the unconventional path can be achieved through hard work. Her father's experience managing racetracks and marketing background gave her exposure to the business world.
While many entrepreneurs seek to capitalize on expanding their offerings to increase revenue, Sam has intentionally kept her business primarily focused on a collection of legal templates she coined the Ultimate Bundle which has generated over $8 million in revenue.
Her weekly newsletter, "Sam's Sidebar," reaches 47,000 subscribers – impressive for a topic many might consider dry. Her secret? What she calls the "broccoli and mac and cheese strategy."
"I consider myself to be the broccoli because a contract or an attorney is something you need. However, everybody just wants mac and cheese. So I use that approach with my audience once they have the legal templates."
'Can you explain your marketing funnel in layman's terms?' I asked.
'I give something to the potential customer in order to invite them in my world, which in this case is a free webinar. After the webinar is completed, they will get a series of emails inviting them to get the Ultimate Bundle.'
When asked about the relationship between money and happiness, Sam offered insights drawn from her own experience. "Money doesn't provide happiness. It certainly makes your life easier. I can pay for someone to do my yard, which makes me happy because I don't have to do it. But did it solve all of my life's problems? Of course not."
Instead, financial success has allowed her to align her spending with her values—purchasing an electric car, supporting the Leukemia and Lymphoma Society with fundraising webinars in honor of her father, and caring for her dad when he was ill.
When asked what advice she would impart on an ambitious person early on in their career, she said to always keep an open mind. It's the same philosophy that led her to discover her successful business.
'I didn't think of my main product when I started my business. I only started it because I listened to the feedback. If I had been closed off to it, I would've missed a big opportunity.'
As we said our goodbyes, I couldn't help but notice the quiet confidence that comes from someone who has built success on her own terms. Sam Vander Wielen reminds us that sometimes our most meaningful success stories begin with noticing where people are already lining up to ask for our help, rather than forcing our preconceived notions of what our path should be.
And perhaps most importantly, she offers a powerful reminder that the business doesn't make you happy - it's learning to find joy in the journey, no matter where the road leads.
Click here to listen to the full interview with Sam Vander Wielen