Jason R. Owens

How to Win in Your First Three Years

Build Your Confidence. Develop Your Judgment. Give Your Business a Stronger Start.

Turn “Can I Really Do This?” Into “I’m Building a Business.”

Starting a business puts something personal on the line.

Your skills. Your ideas. Your savings. Maybe your hope of finally earning a living doing work you love.

Then come the decisions nobody prepared you for. What should you charge? Where should you focus? When should you keep going—and when should you change your approach?

A slow week can feel like a verdict. Someone else’s success can make you question your own progress. You can spend an entire day working and still wonder whether you moved the business forward.

How to Win in the First Three Years helps new business owners understand the experience they are having and become more deliberate about what they do next.

Through guided exercises, discussion, and practical examples, Jason Owens helps participants recognize what they already bring to the business, identify what they need to learn, and build confidence through purposeful action.

Bring the business you are building—and the questions you have been carrying.

Ideal For

• Small Business Centers and SBDCs

• Chambers of Commerce

• Community banks hosting entrepreneur education events

• Economic development organizations

• New business owner programs

• Entrepreneur conferences and business expos

• Trade associations supporting independent business owners

• Maker, creative, and service-business communities

• Organizations helping serious side-business owners prepare for full-time ownership

Best for Events Where Business Owners Are Asking:

• Am I cut out for this?

• How do I know whether I am making progress?

• What deserves my attention when everything feels urgent?

• How do I make decisions without knowing how they will turn out?

• What do I do when something I try does not work?

• How do I stop comparing my beginning with someone else’s established business?

• How do I build confidence while I am still learning?

• How do I give this business a real chance without letting it consume my life?

Audience Takeaways

Participants will leave better equipped to:

1) Recognize the learning curve of business ownership
Identify where unfamiliar responsibilities and missing skills are creating uncertainty—and turn those concerns into specific learning needs.

2) Take inventory of what they already have
Recognize the skills, experience, relationships, and resources they can put to work now.

3) Build confidence through competence
Choose manageable actions that develop ability and provide evidence of progress.

4) Learn from results without making every setback personal
Examine what an attempt revealed about an offer, customer, or approach—and decide what to adjust.

5) Focus on a meaningful next move
Select a practical priority, define a small test, and decide how to assess what happens.

Featured Workshop

How to Win in the First Three Years: Finding Your Footing as a Business Owner

You can be excellent at your craft and still feel inexperienced at running a business.

A skilled tradesperson becomes responsible for estimates, scheduling, and customer conversations. A maker has to think about pricing and sales channels. A creative professional must learn to explain the value of work that feels deeply personal.

The business asks you to grow beyond the work you already know how to do.

In this workshop, Jason helps participants make sense of that transition. Drawing on his work with entrepreneurs and his research on the emotional journey of new business owners, he explores how confidence develops alongside competence.

Participants take stock of their starting point, examine the questions slowing them down, and identify opportunities to learn through action.

Winning begins to take a more useful shape: making better decisions, understanding customers more clearly, developing needed skills, and building a business that has a place in the life they want.

The goal is to leave with a stronger sense of what they can influence—and a practical way to move forward.

What Participants Work On

An Inner Roadmap for New Entrepreneurs

Participants connect the ideas to their own businesses through guided reflection and practical exercises.

They explore:

• What they want the business to make possible in their lives

• Which strengths and resources they can use now

• Where they need more knowledge, practice, or support

• What is keeping them stuck

• Which assumptions they need to test

• What meaningful progress would look like in the next 30 days

Each participant chooses a next step small enough to take and useful enough to learn from.

Why Jason

Jason Owens brings more than 20 years of experience working with entrepreneurs, small business owners, and teams on sales, marketing, business development, and the decisions involved in building a business.

He has delivered more than 40 paid small business workshops, including repeated engagements through North Carolina’s community-college Small Business Center network.

His research on the emotional journey of new business owners informs his understanding of the uncertainty, confidence, and identity changes that can accompany entrepreneurship.

Jason understands how much of the owner comes into the business each day: ambition, experience, expectations, and the private question of whether they have what it takes.

He brings practical business thinking, thoughtful exercises, and humor to help participants develop their abilities and give themselves a clearer path forward.

Workshop Format

An interactive workshop featuring guided exercises, discussion, practical examples, and individual reflection.

Suitable for:

• Standalone small business education events
• Conference breakout sessions
• New business owner programs
• Sponsor-hosted entrepreneur events

Session length and emphasis can be tailored to your audience, schedule, and learning goals.

Best-Fit Themes

• The first years of business ownership
• Entrepreneurial confidence
• The confidence–competence connection
• Moving from skilled practitioner to business owner
• Making decisions under uncertainty
• Learning through practical business experiments
• Choosing priorities
• Recovering from early disappointments
• Building a business that supports a meaningful life