Cracking the Million Dollar Code: Entrepreneurs That Sold Millions (And How You Can, Too)

Less than 10% of new businesses reach $1 million in annual sales within five years. While this milestone may seem difficult to achieve, the entrepreneurs featured here prove otherwise and show you effective methods to get there. Even if you’re just starting out with a laptop and cell phone and nothing more!

From transforming a side hustle into a global research agency to scaling a 7-figure real estate firm in off-hours, their journeys reveal valuable lessons about starting from scratch, perseverance, strategy, and growth.

In this guide, you’ll uncover the strategies that worked, the challenges they overcame, and the insights they gained to help you chart your path toward millions in sales and sustained business success.

Starting the Journey: Side Hustles to Full-Time Success

Building a business while managing a full-time job takes discipline and clear priorities. Many entrepreneurs start small, finding ways to balance their time and focus on steady progress. The following examples show how determination and smart planning can transform a side hustle into a thriving business.

Building Your Business Off-Hours

Justin deMontigny launched PMA Property Group, LLC. by dedicating evenings and weekends to researching real estate opportunities and managing deals. His structured approach enabled him to grow a strong real estate portfolio without compromising the responsibilities of his full-time job.

Tom Shapiro, founder of Stratabeat, Inc. , grew his marketing agency by dedicating early mornings to client projects. This quiet, uninterrupted time allowed him to deliver exceptional work while balancing the demands of a day job.

Richard Kirstein began Strongsize as a small project DBA within his family’s business, Fred David International U.S.A., Inc. He started by selling a single T-shirt on Amazon, using customer feedback to improve the product before expanding operations.

Leslie Jorgensen founded Supporting Strategies, LLC after completing a freelance project to establish financial systems for a startup. This experience sparked the idea for her business, which now supports thousands of small businesses with outsourced accounting, bookkeeping, and operational services.

Josh LaMar co-founded Amplinate after stepping away from his role at Microsoft. During a sabbatical in Paris, a single LinkedIn post announcing his availability for freelance work led to his first client: Meta. This project quickly grew into an international UX research agency.

Whether starting with a single product like Richard or leveraging your expertise like Josh, these stories demonstrate how small, intentional steps can lead to full-time entrepreneurial success.

Tips for Starting Your Journey

• Focus on one core product or service: Starting with a specific offering that aligns with your expertise simplifies your operations and builds trust.
• Dedicate consistent hours to your business: Use early mornings, evenings, or weekends to create momentum.
• Plan your finances carefully: Reinvest early profits into your business to establish a stable foundation and reduce stress.

Focused effort and careful business planning set the stage for long-term growth and success. Entrepreneurs who build their businesses step by step create a solid path toward their first million. (Find our free business plan template here.)

The Power of Self-Funding and Bootstrapped Growth

When launching a new business, there are various LLC funding options. Self-funding gives entrepreneurs the freedom to maintain control and make decisions that align with their vision. Reinvesting profits thoughtfully allows for sustainable growth without the added pressure of external investors or loans.

“Self-funding gives entrepreneurs the freedom to maintain control and make decisions that align with their vision.”

How Bootstrapping Builds a Solid Foundation

Richard used resources from his family’s business to launch Strongsize. Competitive pricing on Amazon attracted customers, while early feedback helped refine his products. Offering bundled T-shirt packages increased margins and improved customer satisfaction, allowing for steady growth with minimal overhead.

Justin reinvested profits from his real estate ventures to grow his portfolio. This approach avoided over-leveraging and focused on long-term value, creating a financially stable foundation for sustained growth. Josh structured Amplinate’s pricing for UX research projects to reflect their value and appeal to high-ticket clients. His projects often required managing international research studies with large teams. While payment delays created cash flow challenges, Josh used detailed financial planning to allocate early profits toward operational needs. This careful approach allowed his team to maintain consistent delivery and continue scaling.

Jeff Nicholson built Tracer Labs, Inc. through a self-funded model, incubating the business within VaynerMedia. Development was funded through profits from VaynerMedia’s media department (which Jeff had spearheaded), allowing Tracer to launch with over $1 million in revenue. Profits were carefully allocated to improve the platform and keep customer acquisition costs low, enabling Jeff and his team to build a scalable and sustainable foundation.

Takeaways for Sustainable Growth

Bootstrapping builds a stable foundation for thoughtful scaling. These principles supported the growth of successful businesses:

• Reinvest early profits thoughtfully: Using profits to fund growth promotes financial stability and reduces reliance on loans.
• Plan for cash flow gaps: Businesses dependent on client payments can benefit from anticipating delays and creating a plan to bridge those gaps.
• Separate finances clearly: Keeping personal and business finances distinct simplifies decision-making and allows for transparent reinvestment.
• Avoid unnecessary debt: Prioritizing financial flexibility supports deliberate, sustainable growth.
• Separate your business finances: Be sure to set up a business bank account in order to separate your business finances from your personal finances.

Patience and discipline are key to self-funding. Entrepreneurs who invest profits back into their businesses create stable foundations that align with their goals.

Breaking Through: How They Made Their First Sale

Reaching your first sale, or your first $100,000 in sales, marks a pivotal step toward building a million-dollar business. Our featured entrepreneurs tailored their strategies to their industries, helping them to secure new business even in the earliest days of their entrepreneurial journeys.

Josh LaMar's High-Ticket Strategy

Josh launched Amplinate with a focus on high-value UX research projects. A single LinkedIn post announcing his availability quickly attracted high-profile clients like Meta, positioning him as an expert in his field. His first project brought in $120,000 and established his premium pricing strategy. From there, the business grew to reach millions in annual revenue.

Josh shares his business-building expertise through an upcoming book designed to guide entrepreneurs to success. Follow the book's launch on his Substack to stay updated, and learn more about his business growth ideas.

Key decisions:

• Positioned services at premium price points ($50,000–$100,000 per project)
• Focused on enterprise clients capable of supporting larger contracts
• Structured payment terms with 50% upfront deposits
• Secured three additional enterprise clients within 60 days

Richard Kirstein's Volume-Based Approach

Strongsize began with a single $24.99 T-shirt sold on Amazon. Richard relied on experimentation and data-driven adjustments to refine his strategy.

Key actions:

• Tested 20 price points in the first month ($19.99–$34.99 range)
• Created bundled packages that increased average order value by 47%
• Improved visibility through clear product descriptions and detailed infographics
• Scaled successful products using targeted Amazon PPC campaigns, achieving a 380% ROI

Within six months, Strongsize reached $8,000 in monthly revenue. Profits were reinvested into inventory expansion, leading to $100,000 in sales by month nine.

Justin deMontigny's Real Estate Sales Formula

Justin combined traditional real estate methods with Airbnb strategies to generate his first $100,000.

Key components:

• Purchased a $200,000 property generating $3,000 monthly in Airbnb revenue
• Focused on undervalued properties with high rental potential
• Followed a formula requiring properties to yield 2% monthly returns in short-term rentals
• Built relationships with real estate agents to access listings early

What Didn't Work

Learning from early mistakes shaped their success:

• Josh faced a pricing challenge at first, charging premium prices even though they were brand new. Their prices were a bit high at first, but over time he worked to find the Goldilocks zone between the highest and lowest price options.
• Richard spent $5,000 testing premium materials before fully understanding his market.
• Justin’s first long-term rental attempt yielded only 0.8% monthly returns.
• Leslie’s early attempt to standardize client packages reduced flexibility, leading to dissatisfaction among some early clients.

Strategies for Scaling and Growth

Scaling a business often requires identifying opportunities, building relationships, and refining one’s marketing. These entrepreneurs illustrate how intentional strategies can support consistent growth.

Seizing Market Opportunities

Adjusting to market shifts can lead to significant growth.

Justin began his real estate journey during the recession, purchasing undervalued properties. As demand shifted, he adjusted his focus to short-term Airbnb rentals and condo development. Justin also used Instagram to feature his properties, attracting tenants and gaining visibility without significant costs.

Richard transitioned Strongsize from wholesale to direct-to-consumer online sales. Selling on Amazon expanded the brand’s reach and provided valuable customer data, which allowed him to refine products and pricing. This led to a loyal customer base and sustainable growth.

Josh launched Amplinate during the pandemic, adopting remote research tools like Zoom to deliver high-quality international studies. This allowed his team to run operations effectively, introducing efficiencies that positioned Amplinate as a reliable global research agency. A single LinkedIn post announcing his availability brought in clients like Meta, further establishing the company’s reputation as a UX research expert. An early article Josh authored on remote research helped position himself as an expert in the field.

Tracer’s first major client, Chase Bank, marked a significant milestone. Jeff’s team earned Chase’s business by delivering clear and efficient reporting that others couldn’t match. This credibility led to additional high-profile clients, including Sanofi Pharmaceuticals and McDonald’s. Jeff refers to this approach as “reputational retention.” By consistently delivering excellent results for early clients, Tracer created a steady stream of referrals and expanded its reach without traditional marketing.

Takeaway: Flexibility and a commitment to quality open doors for growth. Adapting strategies to meet market demands builds resilience and positions businesses for success.

Networking and Relationship Building

Strong relationships are essential for sustained success. Trusted connections generate referrals, collaborations, and long-term partnerships.

Leslie expanded Supporting Strategies by prioritizing client satisfaction and building strong professional relationships. Asking meaningful questions and exceeding client expectations led to steady referrals.

Tom initially built Stratabeat’s client base through referrals from professional contacts. His dedication to delivering outstanding work created a reliable foundation for growth.

Josh’s relationship with Meta stemmed from years of professional collaboration throughout his career. His reputation as a trusted expert paved the way for new opportunities when he and a co-founder launched Amplinate.

Takeaway: Trust and consistency are the foundation of meaningful business relationships. Maintaining these connections supports long-term growth and stability.

“Trust and consistency are the foundation of meaningful business relationships.”

Smart Marketing Strategies

Purposeful marketing connects businesses with the right audience. Combining digital and traditional approaches delivers measurable results.

• Social Media: Justin used Instagram to showcase his rental properties, generating tenant interest and increasing visibility for his real estate business. Josh used LinkedIn to secure his first client.
• Content Marketing and SEO: Tom published comprehensive guides, original research studies, and data-driven articles that attracted organic traffic from Google. This strategy positioned Stratabeat as a trusted resource in the marketing industry.
• PR and Events: Tom also spoke at industry events (as many as 12 in a single year) and participated in webinars and podcasts, reinforcing his agency’s authority and building connections with high-value leads.
• Amazon: Richard relied on Amazon’s platform to grow Strongsize. Clear visuals and detailed product descriptions helped his brand stand out and attract customers.
• Referrals: Jeff prioritized product quality and client satisfaction. Tracer grew through word-of-mouth referrals from satisfied clients, proving that excellent service is one of the most effective marketing tools.

Takeaway: Marketing strategies that focus on customer needs and build trust deliver long-term benefits. Experimenting with channels that align with your audience supports consistent growth. But don’t worry about trying to “boil the ocean.” Focus on what works for your particular audience.

The Importance of Adaptability and Problem-Solving

The road to a million-dollar business is filled with challenges. Entrepreneurs who approach obstacles with determination, resourcefulness, and a focus on their long-term goals often find the most success.

Richard implemented demand forecasting to address inventory management issues. This approach helped Strongsize maintain stock levels without tying up excess capital, keeping operations efficient and costs manageable.

Leslie expanded Supporting Strategies while staying true to the company’s vision. Clear processes and transparent communication helped her grow her team without losing sight of core values.

Josh shifted Amplinate to remote research during the pandemic. Adopting tools like Zoom allowed his team to deliver global research projects without interruption. This shift also positioned Amplinate as a forward-thinking agency capable of meeting client needs in a changing environment.

Takeaway: Success requires a balance of flexibility and strategic planning. Entrepreneurs who respond effectively to change while staying focused on their goals build strong foundations for long-term success.

Overcoming Challenges: Lessons for Aspiring Entrepreneurs

Entrepreneurship has its challenges, but clear strategies can turn them into opportunities for growth. Addressing issues like work-life balance, self-doubt, and scalability helps business owners build resilience.

“Entrepreneurship has its challenges, but clear strategies can turn them into opportunities for growth.”

Finding Work-Life Balance

Balancing professional and personal responsibilities improves focus and productivity. Leslie designed her business structure to align with her goals, creating boundaries and schedules supporting both areas of her life.

Justin used dedicated time blocks to manage his full-time job, family, and real estate ventures. This disciplined approach allowed him to focus on each area without feeling overwhelmed.

Tom made steady progress on Stratabeat during early morning hours (often starting his day at 4am), building his marketing agency while maintaining his full-time job.

With entrepreneurship, be realistic about work-life balance. Starting a business does take hard work. Jeff advises, “If you're thinking about being an entrepreneur, there's a super simple question, and it's how much do you want to sacrifice? Because you're going to have to give a lot for your business and your partners and your company. And if that's something that excites you, then take the risk and try it. Because I would have been very unhappy if I didn't push for the opportunities of what I'm doing and getting the opportunities that I've had with my business partner and my co-workers. And so that would be the biggest thing. If you feel it and you have the desire, then go take a chance and try it!”

Takeaway: Structured time management helps entrepreneurs balance priorities and stay productive without burning out. But be realistic with yourself that starting a new business does take effort and commitment.

Building Confidence

Uncertainty is common in entrepreneurship, but confidence grows through consistent effort and incremental successes.

Josh recalls launching Amplinate during his sabbatical in Paris. Securing Meta as his first client validated his expertise and provided reassurance that his company’s approach was on the right track.

Justin viewed each real estate deal as a step forward, celebrating small wins to build momentum.

Leslie gained confidence from trusted clients, allowing her to refine her business model.

Takeaway: Confidence develops with action. Celebrate milestones, learn from challenges, and trust in the skills and expertise that make your business unique.

Delegating to Scale

Scaling requires identifying tasks that others can manage, allowing business owners to focus on growth and strategy.

Justin collaborated with his sister to manage operations in his real estate ventures. This partnership freed him to explore new opportunities while maintaining efficiency.

Richard entrusted Strongsize’s digital ad campaigns to a media agency. Delegating this responsibility allowed him to refine marketing strategies and concentrate on product development.

Josh expanded Amplinate into a global research agency by hiring a diverse team across countries like Brazil and the Philippines. He focused on building a team that could adapt to cultural differences while staying aligned with the company’s mission.

Tom outsourced all accounting work. This freed him up to focus on keeping clients happy and marketing the business.

Takeaway: Building a strong team and delegating responsibilities supports sustainable growth and gives entrepreneurs the freedom to focus on larger goals.

Proven Strategies to Build a Million-Dollar Business

Achieving millions in revenue requires clear strategies, deliberate actions, and consistent effort. The entrepreneurs we’re featuring show how thoughtful decisions drive meaningful results.

Start Small and Refine Your Strengths

Launching with a focused offering builds expertise and trust. Starting small allows you to test ideas, adapt, and grow with intention.

Josh began Amplinate with his co-founder with a single project for Meta, a client he secured through a professional relationship. Operating under an LLC structure, this project helped them fine-tune their processes and showcase the agency’s ability to deliver high-quality UX research.

Richard started Strongsize by selling one T-shirt on Amazon. This simple approach allowed him to gather customer feedback and improve his product without stretching resources. Optimizing listings with clear descriptions and engaging visuals improved visibility and sales.

Leslie used the LLC structure for Supporting Strategies to provide liability protection as the business scaled. Her initial freelance project offered valuable insights into client needs, shaping a focused service offering in outsourced accounting and bookkeeping.

Takeaway: Focus on one clear offering to build credibility and refine your approach. Early experiences lay the foundation for sustainable growth.

Reinvest for Strategic Growth

Reinvesting profits creates opportunities for sustainable growth and builds a strong financial base for expansion.

Justin reinvested earnings from his real estate deals to acquire more properties under PMA Property Group LLC. The LLC structure provided a tax-efficient framework while minimizing personal risk. Careful reinvestment helped Justin grow a profitable portfolio without relying on excessive debt.

Tom used early revenue from Stratabeat to hire key team members, upgrade infrastructure, and travel around the U.S. speaking at industry conferences. These investments strengthened the agency’s ability to deliver value and secure new clients for longer-term growth.

Jeff funded Tracer’s growth using profits from VaynerMedia’s media department. Operating under its initial LLC business structure, Tracer maintained full control over decision-making while delivering innovative solutions to clients like Chase. (The company later transitioned to an incorporated entity in alignment with the company’s growth.) Reputation-building became a key growth driver, with satisfied clients advocating for the platform’s value.

Takeaway: Thoughtful reinvestment strengthens operations and creates growth opportunities without unnecessary risk.

Build Trust Through Authentic Relationships

Strong relationships open doors to referrals, partnerships, and collaborations. They are built on mutual trust and delivering real value.

Leslie built a reliable referral network by asking thoughtful questions and delivering personalized solutions. This approach created trust and consistent growth for Supporting Strategies.

Josh credits Amplinate’s success to long-standing professional relationships. His first project for Meta resulted from mutual respect and trust, paving the way for larger opportunities.

Takeaway: Build genuine relationships that provide value. Long-term connections support growth and open opportunities at every stage of your business.

Adapt to Challenges and Change

Flexibility helps entrepreneurs overcome challenges and uncover new opportunities. Josh transitioned Amplinate to remote research during the pandemic, allowing his team to deliver high-quality results while expanding their global reach.

Richard shifted Strongsize from wholesale to direct-to-consumer sales, which better aligned with customer needs and gave him more control over growth.

Takeaway: Embrace challenges as opportunities to refine your strategy and position your business for success.

How LLC Attorney Supports Your Million Dollar Business Journey

Starting a business with a strong foundation creates opportunities for long-term growth. Entrepreneurs face challenges such as compliance, liability, and scalability, but LLC Attorney simplifies these complexities so you can focus on success.

• Fast and Professional Services: Business formation involves many moving parts. LLC Attorney handles LLC filings, EIN filings, and compliance, saving you time to focus on building your business.
• Privacy and Asset Protection: Protecting personal assets is essential as your business grows. Supporting Strategies benefited from the liability protection provided by its LLC structure, giving Leslie the confidence to expand her operations. PMA Property Group LLC used the same framework to minimize risks while scaling Justin’s real estate portfolio.
• Expert Guidance: Legal and financial challenges can feel overwhelming. LLC Attorney provides support with operating agreements, tax filings, and registered agent services.These services help businesses focus on growth while maintaining a strong foundation.
• Legal Consultation: If you’d like to speak with one of our business attorneys about your legal questions, you can book a consultation here.

Successful businesses grow from thoughtful planning and solid foundations. LLC Attorney simplifies business formation and compliance, helping you stay focused on achieving your goals.

Take the First Step Toward Your Success

Every business starts with a vision. Entrepreneurs who align their goals with a solid foundation create businesses that achieve significant milestones. Proper planning and a commitment to growth have helped the entrepreneurs featured here reach millions in revenue. You can do the same.

Ready to start and grow your business? Ready to achieve millions in sales? Start the process by forming an LLC today.