Third Shift Entrepreneur

Do you feel stuck in your 9-to-5, dreaming of pursuing a business idea but unsure how to start without risking your steady income?

1. Your passions and talents are the foundation for your business idea

Many people struggle to identify a business idea, often trying to follow trends or replicate someone else’s success. However, Todd Connor emphasizes that the best business ideas emerge from personal passions, talents, or even unique problems that intrigue or bother you. These are the raw materials for creating something meaningful and sustainable.

In the book, this concept is introduced through Matt's interaction with Kenneth, a rideshare driver gathering insights for his corporate retreat business. Through Kenneth’s example, Matt learns that his professional and personal interests can provide clues to his ideal business. The key takeaway is to deeply explore what fascinates you because this foundation will fuel your motivation in the long term.

As part of this discovery process, Connor suggests making a list of obsessions—like hobbies, frustrations, or recurring thoughts. Revisiting that list regularly and exposing yourself to new experiences expands your perspective, helping you connect your ideas creatively.

Examples

• Kenneth using rideshare conversations to research corporate retreats.
• The observation that obsession drives entrepreneurs who start businesses about which they’re deeply passionate.
• Matt jogging after work to see his world differently and spark fresh ideas.

2. Your day job can support your side hustle

A common hesitation for aspiring entrepreneurs is the fear of leaving a stable job for an uncertain venture. Connor argues that your day job can serve as a training ground and financial safety net for your business while it’s still developing.

This idea becomes clear through Yisel’s coffee-roasting journey. Her full-time marketing role sharpens her skills for promoting her coffee business, while her night job at a coffee shop provides access to roasting equipment. By using her work environments effectively, she saves money and hones her business operations without giving up stability.

Matt applies this principle by seeking clients in industries he’s passionate about, blending entrepreneurship into his consulting role. This approach allowed him to provide value to his employer while carving out a niche for himself.

Examples

• Yisel uses her coffee shop job to perfect her craft while earning extra income.
• Kenneth combines rideshare driving with business research for future retreats.
• Matt negotiates with his boss to work with outdoor industry clients while keeping his current responsibilities.

3. Think small: Start testing your idea with minimal resources

Many aspiring business owners feel paralyzed by the perceived need for significant investment or grand planning. Contrarily, Connor stresses the importance of starting small, running experiments, and observing early feedback.

This idea is illustrated by Alberto, whose original vision for a large-scale VR escape room business began modestly in his garage. With basic resources and a focus on their primary goal—creating a fun, thrilling experience—he and his wife quickly gained traction and market validation.

Starting small not only reduces risk but also allows you to learn efficiently. Testing ideas in their simplest form can illuminate opportunities for growth or adjustment without overcommitting upfront.

Examples

• Alberto converting his garage into a test site for his VR escape room idea.
• Using market interest as a guide for refining and expanding their offering.
• Other group members urging each other to take swift, small steps over endless planning.

4. Adapt your model without abandoning your mission

Flexibility is vital when bringing business ideas to life. Connor shows that remaining clear on your mission while being open to changing its execution is key to eventual success.

Kim’s story demonstrates this. She wanted to help foster care youth transition to independence, but through research and sponsor feedback, she found it best to narrow her focus to housing for young women. This adjustment allowed her to secure funding and ensure her nonprofit made a tangible impact.

This insight reveals that staying mission-driven often requires creative pivots to get your initiative off the ground and keep it sustainable over time.

Examples

• Kim refining her nonprofit’s mission to focus on housing for young women.
• Alberto pivoting from running a VR escape room to consulting on similar experiences.
• Matt modifying his role in his business partnership to prioritize outdoor adventures he loves.

5. Internships offer valuable hands-on learning

Treating inventive business opportunities as internships creates a chance to explore ideas in a low-pressure environment. This mindset reframes side hustles as experimental learning labs rather than high-stakes commitments.

Yisel uses her coffee shop job as an "internship" to master coffee roasting, retail dynamics, and customer preferences. Similarly, Matt explores whether his consulting strengths align with his outdoor passion by finding relevant clients. These approaches make the journey toward entrepreneurship feel more approachable.

The internship mindset transforms curiosity into action, allowing you to gain experience before fully committing to a business.

Examples

• Yisel learning from customers and retail processes at her coffee shop job.
• Matt testing his skills on outdoor industry clients before starting his company.
• Chad earning his partner’s support by sharing a mutual interest in antique maps.

6. Build your network and find mentors

No entrepreneur succeeds alone. Networking and mentorship are critical components of growing your business. Connor emphasizes the value of communities like the Third Shift Entrepreneurs, which provide shared knowledge, collaboration, and moral support.

Matt benefits from people like Regis, who encourages storytelling and experimentation, and his boss Saul, who guides him in balancing his new interests with his day job. These relationships help Matt advance his goals while avoiding missteps.

Building relationships not only gives you access to guidance but also introduces you to people who can advocate for your idea.

Examples

• Kenneth and Matt exchanging professional strategies during rideshare chats.
• Matt gaining trust and support from his boss Saul.
• Alberto’s business growing through word-of-mouth from a connected community.

7. Leverage feedback to refine your approach

Customer feedback often reveals surprising opportunities. Observing how the market reacts—or doesn’t—is integral to shaping your business.

Alberto’s VR project drew attention not just for its entertaining experience but for its design potential, leading him to pivot into consulting. Similarly, Yisel relied on customer preferences to fine-tune her coffee blends. Always viewing feedback as a resource can uncover new perspectives.

Staying attentive to reactions allows entrepreneurs to anticipate needs and adjust accordingly.

Examples

• Alberto transitioning from escape rooms to consulting based on feedback.
• Yisel perfecting her coffee blends by listening to customers.
• Matt exploring niche consulting ideas after hearing from outdoor industry clients.

8. Your business should work for your life goals

Entrepreneurship is about more than financial success; it’s about building a life that aligns with your goals and values. Connor highlights that understanding your desired outcomes will shape every decision along the way.

Matt achieves this by finding balance through a business partnership that lets him enjoy the outdoors while contributing strategically. Knowing your endgame ensures your business supports the life you envision.

A purpose-driven approach keeps you focused, preventing burnout or misalignment with core priorities.

Examples

• Matt’s outdoor business aligning with his passion for adventure.
• Alberto’s pivot to consulting, giving him more flexibility and income.
• Kim eventually transitioning full-time to her nonprofit once it became viable.

9. Apply urgency to move from dreaming to doing

Taking small, quick steps toward your idea creates momentum. Connor’s mantra for entrepreneurs is simple: action beats perfection. Without urgency, big ideas risk remaining untested dreams.

The Third Shift group exemplifies urgency by holding each other accountable for making immediate progress. Alberto’s rapid creation of the VR garage escape room or Yisel’s on-the-job learning are products of this fast-paced, action-driven mindset.

Progress happens when you prioritize action over analysis paralysis. Small moves today lead to meaningful results down the road.

Examples

• Alberto launching his escape room in just a few months.
• Matt switching gears to outdoor industry clients.
• Group meetings pushing members to test and refine ideas constantly.

Takeaways

1. Create a list of your obsessions—passions, talents, or recurring frustrations—and actively explore how they could inspire a business idea.
2. Utilize your current job as a platform to research, practice, and refine your entrepreneurial skills without sacrificing financial security.
3. Take small, immediate actions to test your ideas, and stay open to pivots that align with your larger mission.