From Side Hustle to CEO: Financial Strategies for Entrepreneurs

In this episode of Pros and Conversations, hosts Peter Reynolds and Damon Adachi explore what it takes to turn a passion project into a full-time business.

They’re joined by Steve Ackroyd, a seasoned CPA with over 20 years of experience helping entrepreneurs transition from side hustles to sustainable success. Steve shares key insights on cash flow management, tax planning, and knowing when to incorporate—essential steps for any new business owner.

Together, they discuss the value of financial discipline, trusted advisors, and planning for growth—whether hiring staff or preparing for expansion. Throughout the episode, Peter and Damon emphasize that while you may be in business for yourself, you don’t have to do it by yourself.

A must-listen for anyone ready to turn their passion into a sustainable enterprise.

Chapters

• 0:00 Introduction to Pros and Conversations
• 0:15 Turning Passion into Business
• 0:26 Introducing Steve Aykroyd, CPA
• 0:37 Challenges in the First Three Years
• 0:57 Importance of Professional Advice
• 1:25 Peter's Journey from Side Hustle to Business
• 1:54 Welcoming Steve Aykroyd
• 2:22 Steve's Background and Practice
• 3:21 Steve's Leap to Start His Own Firm
• 4:15 Common Financial Mistakes by New Entrepreneurs
• 5:08 Personal Anecdotes on Financial Planning
• 7:21 Importance of Business Education
• 8:03 Should Entrepreneurs Educate Themselves?
• 9:14 Incorporation Decisions
• 11:44 Planning Your Exit Strategy
• 13:02 Cash Flow Management Tips
• 14:21 Example of Advising Against Incorporation
• 16:17 Managing Cash Flow on a Shoestring Budget
• 21:04 Mid-Episode Sponsor Messages
• 22:40 Importance of Accountability in Business Finances
• 25:42 Choosing the Right Accountant
• 28:42 The Role of Referrals in Finding Professionals
• 30:30 Understanding Audits and Compliance
• 33:37 Avoiding Red Flags with CRA
• 36:16 Growing Your Business: Taking the Next Leap
• 40:11 Final Advice for Aspiring Entrepreneurs
• 41:42 Closing Remarks and Networking Importance
• 43:22 End of Episode