🐧 Bootstrapping a 6-figure wellness brand | Jamie Lee

Spotlight: From Teacher to Tech Professional to 4-Time Founder
August 20, 2023

This Aussie entrepreneur in Singapore bootstrapped a fast-growing journal company.

Meet Jamie Lee, founder of Chai Sunrise. 🌄

Today in 10 minutes or less, you’ll learn:

  • 👩‍🏫 How Jamie went from teacher to techie to 4-time founder
  • 📔 Choosing to bootstrap Chai Sunrise, hitting 6-figure revenue
  • 🤔 Deciding to go full-time vs part-time
  • 📣 Finding customers via network, social media, and community
  • 🫶 Mistakes and advice for new bootstrappers

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📔 Bootstrapping a 6-figure wellness brand | Jamie Lee

Jamie Lee is the founder of Chai Sunrise, a wellness company, where she is focused on helping others discover mindfulness and escape the daily grind through their guided journals. She has a background in education and has been invited to speak at top companies such as Netflix, Salesforce, Barclays, TEDx, Unilever, and LinkedIn.

Her commitment to making a difference has earned her several prestigious accolades, including the 30Under30 Anthill Young Entrepreneur Award, WYSE Global Youth Best Work Experience Provider, Australia's Favourite EduTech Startup, and the ASG Inspirational Teaching Award.

👩‍🏫 Tell us about your career journey going from teacher to tech professional to starting businesses.

As a teacher, I cherished the moments spent nurturing young minds, fostering creativity, and witnessing the spark of inspiration in my students' eyes. However, deep within me, I yearned for a broader canvas to express my creativity and touch the lives of individuals beyond the four walls of a classroom.

Opportunity came knocking when I was offered a position at Carousell. It was a world brimming with cutting-edge projects, collaborative brilliance, and a constant drive to push boundaries. Immersed in this dynamic environment, I felt a sense of purpose and a newfound understanding of the transformative power of technology.

Yet, amidst the whirlwind of my tech career, I started hearing this quiet little voice calling me to venture into an unexplored realm — an invitation to use my skills and passions to create something tangible, something that would bring joy and inspiration to others.

Guided by my teaching background and fueled by my own transformative mental health journey, I took the leap and founded my own wellness company. My goal was to craft journals that would not only be beautiful but would also inspire personal growth, reflection, and creativity.

Looking back on my journey, I realize that it was never just about the career shifts or the entrepreneurial endeavor—it was about following my passion, embracing change, and taking the leap of faith to create something meaningful. Each step along the way, from teaching to the tech industry and now as a journal entrepreneur, has shaped me into the person I am today.

🚀 You chose to bootstrap your current business, Chai Sunrise. How did you weigh the decision to bootstrap versus raise outside funds?

Chai Sunrise is a small-scale venture — with six-figure revenue in its first year. It didn't demand extensive capital investments or complex infrastructure. By bootstrapping, I could start lean, keep costs low and focus on organic growth.

Additionally, I reflected on the potential trade-offs of seeking external funding. While raising funds from investors could provide an injection of capital, it often comes with strings attached. Investors typically seek a stake in the business or expect a say in decision-making processes, which might compromise my autonomy and the creative direction of Chai Sunrise. Bootstrapping allowed me to retain full ownership and decision-making authority.

Another factor I considered was the timeline for growth. Bootstrapping might lead to a slower pace of expansion initially, as resources are limited. However, it also encouraged resourcefulness, innovation, and careful financial management. By building a solid foundation step by step, I could establish a sustainable business model that wouldn't be reliant on external funding or risk running into financial difficulties down the line.

🛠️ You have started four businesses — both as a side hustler and full-time operator. How did you decide when to work on the business on-the-side vs full-time?

I evaluated the business's financial viability, assessing whether it was generating consistent revenue and had the potential for sustainable growth.

The results were promising, as the business managed to generate over SGD $15k in two weeks during its pre-launch phase. This early success provided the necessary funds to cover inventory expenses. Moreover, the business successfully established partnerships with more than 5 retail establishments, demonstrating its potential for growth and broad appeal in the market.

Personal circumstances played a significant role as well. I considered factors such as financial stability, responsibilities, and obligations. It was important to have a safety net in place, ensuring I had enough savings or alternative income streams to support myself during the transition.

However, it's important to note that each business and situation is unique. The timing and circumstances for transitioning to full-time work on a business will vary based on individual factors. It requires careful evaluation, financial preparedness, market conditions, and personal considerations.

📣 How did you find your first customers for Chai Sunrise?

To kickstart Chai Sunrise's customer acquisition, I employed a multi-faceted approach:

  • Tapped into my personal network, reaching out to friends, family, and colleagues who I believed would resonate with Chai Sunrise's offerings. Their support not only became the foundation of our initial customer base but also provided invaluable feedback to refine our product and shape our brand.
  • Harnessed the power of social media to establish a strong online presence. Through Instagram, we ran pre-launch campaigns, and built a mailing list to showcase Chai Sunrise's unique value proposition. This allowed us to engage with potential customers, building anticipation and excitement around our brand.
  • To amplify our visibility, we actively engaged with online communities and collaborated with wellness & mindfulness influencers. Notable collaborations include influencers like Iman Fandi Ahmad, Fiona Fussi, Tara Bakalian and Bernadette Ong. By fostering relationships and participating in relevant discussions, we cultivated trust and expanded our reach to an audience passionate about mental well-being and self-care practices.
  • As Chai Sunrise gained momentum, positive reviews and testimonials became important. With every satisfied customer sharing their experience, a wave of social proof swept across our brand, drawing in new customers and attracting retailers who were eager to collaborate with us.

💫 If given the opportunity, what changes would you have made to your business?

If given the opportunity, one change I would have made to my business is to explore a bigger market outside of Singapore.

While starting out, I may have initially focused on a specific niche or local market. However, as the business grew and evolved, I realized the potential for expansion into larger markets like the US or UK.

By identifying and targeting a broader audience, I could have tapped into new customer segments and increased the business's reach and revenue potential. Expanding into a bigger market would have allowed for greater scalability and opened up new opportunities for growth and success.

🫶 What advice would you give to someone looking to bootstrap a business?

Here are 5 key pieces of advice to consider as you embark on your bootstrapping journey:

  1. Start with a Clear Vision: One approach is to start with a vision board. I gather images, words, and visuals that represent my aspirations and goals for the future. This helps me clarify my vision and visualize the direction I want to take. Another valuable exercise is conducting a SWOT analysis (Strengths, Weaknesses, Opportunities, Threats). By assessing the internal strengths and weaknesses of the business or myself, as well as the external opportunities and threats in the market, I gain a better understanding of where my core competencies lie and how I can leverage them to achieve my vision.
  2. Focus on Core Competencies: With limited resources, it's crucial to prioritize and focus on your core competencies. Identify the key strengths that set your business apart and concentrate your efforts on those areas. Avoid spreading yourself too thin or pursuing too many directions simultaneously.
  3. Embrace Lean Principles: Adopt a lean approach to your business operations. Minimize unnecessary expenses, avoid excessive overhead, and prioritize investments that directly contribute to your growth and value creation. Make informed decisions based on real data and customer feedback.
  4. Prioritize Cash Flow: Cash flow is the lifeblood of any business, especially when bootstrapping. One resource that was particularly helpful to me was learning from my ex-colleague about financial modelling. He had a strong background in finance and kindly shared his knowledge and expertise, guiding me through how to monitor cash flow effectively.
  5. Nurture Customer Relationships: Your customers are your most valuable asset. Focus on building strong, lasting relationships with them. Provide exceptional customer service, listen to their needs, and continuously strive to exceed their expectations. Satisfied customers can become brand ambassadors and a source of valuable referrals.

🏠️ Where can we go to learn more about you?

You can visit our website or reach out to me directly via email, as I'm always open to connecting with curious minds and engaging in meaningful conversations.

🌐 Beyond your borders

🇸🇬 Singapore regulators are among world’s first to agree to stablecoin regulation.

🇺🇸 This in-demand, remote freelance job pays up to $250 an hour, doesn’t require a degree, and demand has increased despite AI.

🇦🇺 With foreign direct investment on the decline, China announces they’re allowing 50 percent foreign ownership of VPN services.

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📆 How I can help

That’s all for today!

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Dexter Zhuang

Dexter is the founder of Money Abroad, an online education platform helping high-performers design their independent money path. He has 10+ years of experience building products and teams at public companies (Dropbox) and scaling startups (Xendit) across the US, Asia, and Latin America. His work has been featured in global outlets like Business Insider, CBS, US News & World Report, and Tech in Asia. He graduated from Dartmouth College.

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