Every entrepreneur has a unique journey, often filled with twists, turns, and challenges that shape not only their business, but their life—here’s how my path from side hustles in the 1990sto tax expertise unfolded.
In high school, entrepreneurship was not on my mind. My dream career back then was to become a police officer, but strict requirements—like being over six feet tall, prioritization of minorities, and French fluency for the RCMP—meant my applications were declined.
Adding to the challenge of find my direction, the high school guidance counselor discouraged me to pursue a post-secondary education in business, and suggested I consider going into the trades.
While trades are admirable, I wasn’t the handy type. Thankfully, my parents believed in me when others didn’t. Their encouragement to follow what I felt was right became a lesson I’ve carried my entire adult life, and even passed on to my own kids.
Post-Secondary Education to the Business World
Despite the guidance counselor's advice, I pursued a post-secondary business education.
In 1989, I entered the workforce, stepping into the business world with an entry-level inside sales role at a local industrial supply company that would become the foundation of my corporate career. I grew up within this company over the next 16 years and have so many amazing memories.
First Introduction to the World Wide Web
In 1991, I remember presenting a formal business case to the company president, requesting approval for dial-up internet access (commonly referred to as "access to the Information Superhighway") at my desk.
I became the first employee in the company to have dial-up internet access and an email address. Can you imagine?
I was that eager young professional, fascinated by the wonders of technology and the World Wide Web, embracing every bit of it at K&D.
Back then, in the workplace, fax machines had just replaced telex machines as the “high-tech mode of communication,” pagers were the go-to method for business messaging, and we were still years away from introducing cell phones—let alone fully understanding the vast potential of what "the internet" would eventually become.
The Early Days of the Internet
In the early 1990s, the internet was a mystery to most, with only 9% of households having access. Platforms like social media or digital payment systems were non-existent, and Google—a today's most common search engine—wouldn't even launch until 1998, remaining relatively unknown for several years.
Commercials like the below 1995 AOL ad captured the wonder and uncertainty surrounding this new technology. It presented the internet as a tool that could simplify life, but it also had to explain how it worked—emphasizing its ease of use and promoting offers like “10 free online dialup hours” to encourage people to explore its possibilities. For many, the internet was still a strange and intimidating concept.
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During those years, from my cubicle at work, I developed multi-million-dollar national sales accounts with the Federal Government by becoming an early adopter of their online public tendering process.
That sales experience became one of the key moments that first inspired me to pursue my own entrepreneurial journey on the internet.
First Step into Entrepreneurship: Online Venture
In 1998, at 29 years old, I took my first leap into entrepreneurship by starting a part-time, home-based online business. With limited resources, I assembled a desktop computer from used parts I could find, and taught myself HTML coding and SEO (search engine optimization), which allowed me to build a website to connect with clients from around the world.
My First Big Tax Write-Off Missed Opportunity
I recall in the early 2000s, the company I worked for had supported the staff in an “employee purchase plan” of personal computers. While I already had a computer, the payment plan option was a great way to get a better computer at home to support my home-based business.
Computers in those days cost about $5,000 (about $7,400 in today’s value)—a significant expense at the time. While it was for my home business, I didn’t realize it qualified as a tax-deductible expense. Unfortunately, my accountant who did my taxes never pointed this out, and I missed out on valuable tax savings.
By the early 2000s, my home business was generating $5,000 per month (equivalent to about $8,000 today).
Despite this success, I unknowingly left tens of thousands of dollars in home-based tax write-offs on the table, simply because I didn’t understand the tax rules—and it was never explained to me.
Durings those years my home business was doing well, I had the dream of walking away from my job and being self-employed working from home, but unfortunately unexpected life’s challenges that were lurking around the corner, forced me to put this dream on hold.
A Challenging Transition—Family First
In 2004, my life took an unexpected turn when I accepted a job offer from a competitor that required relocating to another province. I left K&D, where I had started in 1989, to take on a much larger corporate role.
What I hoped would be a fresh start for my family quickly became one of the darkest personal periods of my life.
Shortly after the move, my personal situation worsened. I gained full custody of my three young children, faced a marital breakdown, and eventually declared personal bankruptcy.
Balancing these challenges with a demanding new corporate role left me no choice but to set aside my home-based business to focus on stability. I took my website offline and even changed my phone number.
With three young kids, I appeared to be managing both my family and a demanding corporate career—traveling across North America for business two weeks each month—but behind the scenes, I was doing everything I could just to hold it all together.
A Wake-Up Call: Overwhelmed with Life
By late 2006, just weeks before Christmas, I hit rock bottom. Exhausted by work and life’s demands, I struggled to summon the energy to go to the office that day.
That same year, my bankruptcy was finally cleared, and I finalized my divorce. The emotional toll of career pressures, constant work travel, single parenthood, and the looming holiday season weighed heavily on me. I was completely drained—unable to function.
It was a critical day at work. Board meetings were scheduled to discuss corporate restructuring, budget adjustments, and layoffs as the early effects of the Great Recession began to hit. But all I could do was crash. I lay down on the couch and fell asleep. When my office called to ask if I was coming in, I simply said, “No, not today. I can’t make it.” I was so overwhelmed, I couldn’t even get up.
When I woke up later that morning, I made a promise to myself: my kids needed me to be strong. I had to pull it together for them—they had no one else to rely on.
That promise became a turning point. It gave me the resolve to rebuild my life and eventually led me back to the entrepreneurial dream I had put on hold years earlier. Just a few years later, I started small—with a side hustle—and began to reshape my future.
My Income Tax Savings Breakthrough Moment
By 2008, I felt the itch to start a side business again. I missed the entrepreneurial spirit of running my own business. This time, I was determined to approach things differently—especially when it came to managing my time and creating an income.
When tax season rolled around in early 2009, I decided to take a completely fresh approach to filing my taxes. I sat down with my pile of receipts, categorized every expense, and did my research to ensure I claimed everything I legally could.
The result? A $6,600 refund. Compared to the $5,000 I owed in each of the previous two years, it was a $13,600 turnaround. That experience opened my eyes to just how much I could save with a side business by following the right tax strategies.
That refund wasn’t just a financial win—it inspired me to dive deeper into learning everything I could about tax write-offs for home-based businesses. Little did I know, those lessons would eventually shape the way I help others today.
A Major Life & Career Shift - Termination Letter Arrived
In 2010, I was faced with my corporate role being terminated due to a downsizing and merger caused by the impacts of the Great Recession.
Suddenly, the steady paycheck I’d relied on for over two decades was gone.
As a single dad, I faced some tough decisions. Continuing in my career would require relocating across the country—or possibly even out of the country.
While I had started my home-based business two years earlier, it wasn’t generating enough income to fully support myself and my three kids. Still, there was a small spark of opportunity: the chance to leave my corporate career behind.
For years, I’d dreamed of being my own boss, working from home, and having more time for my kids. Now, I had an opportunity to make that dream a reality.
It wasn’t an easy decision, but in the end, I took the leap—determined to create something better for me and my family.
Finding My Entrepreneurial Focus
After leaving my corporate job, I dove headfirst into entrepreneurship, determined to create a successful path that could support my family.
Between 2011 and 2013, I fell into the serial entrepreneur trap, trying my hand at several ventures that seemed full of potential.
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My biggest challenge? Each venture lacked the attention and focus it needed to reach its full potential—I was spreading myself too thin. Ironically, I found myself working harder as an entrepreneur than I ever did as a corporate executive.
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One of my larger ventures was a brick-and-mortar store. With an $80,000 investment, I believed it was a great business opportunity at the time.
The reality? Running a retail storefront demanded significant time, financial resources, and constant navigation of city compliance requirements. In the early days, I felt tied to the store every waking hour. It wasn’t the self-employed freedom I had envisioned.
By early 2014, I made the tough decision to close the store, sell off its assets, and refocus solely on my home-based business. While the store operated profitably, closing it meant taking a significant financial loss. Despite this, it was the right decision—allowing me to concentrate on building the kind of life and business I had always wanted.
The Struggle of Bookkeeping & CPAs
During my time as a serial entrepreneur, one thing that caught me off guard was just how overwhelming bookkeeping could be when managing multiple, distinct business ventures. At one point, I was running three businesses—a home-based business, a storefront, and a B2B consulting gig. Each required its own set of profit-and-loss statements, and keeping up with them felt like a full-time job in itself.
I hired bookkeepers, CPAs, and even a tax lawyer at one point, hoping they could provide the support I needed. Unfortunately, most didn’t take the time—or lacked the interest—to fully understand the unique needs of my businesses. I ended up spending a significant amount of money on accounting services and receiving bad advice, which often left me feeling even more confused and frustrated.
Turning Frustrations Into Solutions
With the other two businesses closed and my home-based business as my primary focus, I realized it no longer made sense to rely on outsourcing bookkeeping and tax services.
I decided to take matters into my own hands, learning everything I could about claiming tax write-offs, becoming audit-proof, and filing my own taxes.
Over time, the tools and strategies I developed became the foundation for everything that followed in my journey. Little did I know, these solutions would soon help others as well.
Finding a New Purpose in the Experience
As I shared my bookkeeping experiences and tax write-off strategies with other entrepreneurs, I discovered just how much this type of guidance was needed within the home-based business community.
Over time, my reach expanded. I connected with hundreds of entrepreneurs across North America, answering questions and sharing strategies that worked for both the Internal Revenue Service (IRS) and the Canada Revenue Agency (CRA).
What began as a personal need to take control of my own business evolved into something much greater—a mission to empower home-based entrepreneurs to feel confident in managing this often-overlooked aspect of their businesses.
A Tax Reassessment: Objection Battle and Victory
In 2015, I faced a tax challenge where I was reassessed three years of my tax returns, claiming I owed over $15,000 in back taxes, interest, and penalties.
While the amount was a complete shock, I was confident in my record-keeping and knew the reassessment was incorrect.
Determined to fight back, I submitted an objection letter outlining the errors in their assessment. Months later, my objection was denied. Undeterred, I submitted a second, even more detailed objection, but after months I received another letter advising it too was rejected.
Seeking Expert Advice
Searching for answers, I consulted a former tax collector and advisor. After reviewing my case, he painted a bleak picture, stating that after two failed objections, my chances of ever overturning the decision was slim. Despite his warning, I refused to give up.
Putting My Best Foot Forward
With renewed determination, I decided to handle the third objection myself. I meticulously prepared a very detailed document including supporting documents—all labeled and cross-referenced. I shipped it to the government in a box as thorough I was submitting a legal affidavit, prepared as if I were heading to court.
Victory Against the Odds
Six months later, a letter from the government arrived. After reviewing my third objection package, the decision was overturned, canceling the $15,000 balance. I had won!
This victory wasn’t just a financial relief—it reinforced the confidence in my record-keeping systems and the ability to self-advocate against the government tax authorities.
Family Challenges, Setbacks, Resilience and New Beginnings
A Life-Altering Diagnosis
In 2017, my wife’s sister was diagnosed with stage IV glioblastoma, an aggressive brain tumor. After emergency surgery, she moved in with us, and as the one working from home, I became the primary caregiver—managing medical appointments, treatment schedules, organizing medications, and navigating the complexities of the healthcare system.
Balancing Family and Business
For the next 15 months, my days revolved around supporting her while juggling the dynamics of a growing family. The relentless demands pushed me to my limits, forcing my home business to take a backseat.
This period tested every part of my life—putting a strain on my marriage, challenging the resilience of the family, and leaving little room for my own self-care.
A Turning Point in Perspective
By late 2018, after my sister-in-law’s passing, I was emotionally drained, and my home-based business income had declined significantly.
Looking back, this chapter taught me an invaluable lesson: a home-based business offers an extraordinary gift—the freedom to prioritize family during emergencies. It also underscored the importance of building passive income over active income in a business.
With the need for income, the idea of returning to my corporate career crossed my mind, it wasn’t an option I was willing to entertain. Deep down, I knew I couldn’t give up on my entrepreneurial spirit. It was time to rebuild and refocus on the dream I had worked so hard to achieve over the previous years.
The Creation of Home Business Tax Secrets
A Surprising Start
During this time, I rebranded a Facebook group I had created a few years earlier, renaming it Home Business Tax Secrets.
Within the group, I found inspiration to share practical bookkeeping tips, challenges with tax preparers, and strategies for maximizing tax write-offs and audit-proofing records.
A Tax Opportunity Emerges
As I continued supporting the Facebook group community, I uncovered a deeper issue: most home-based entrepreneurs lacked reliable, tailored tax guidance.
Members frequently shared stories of receiving poor tax advice, missing out on significant tax savings, being given incorrect or incomplete guidance, and ultimately overpaying their taxes.
What started as a small Facebook group eventually grew into a thriving community with over 1,000 members—dedicated to empowering home-based entrepreneurs with the knowledge they needed to succeed.
The rapid growth of the Home Business Tax Secrets Facebook group highlighted the need for more comprehensive resources.
Turning a Tax Write-Off Passion Into a System
In 2019, I transformed years of informal tax advice into a formal, structured offering: an online course originally titled Home Business Tax Secrets Course & Productivity System.
When I launched the course, I knew exactly what home-based entrepreneurs needed to gain the tools, knowledge, and confidence to succeed—because I had been in their shoes. This course, combined with my personalized coaching, has created countless success stories, saving individuals thousands of dollars per year on their taxes.
The course quickly gained recognition as the system that’s helped home-based business owners save tens of thousands in income tax dollars.
For example, one participant used the knowledge from the course to re-file her income taxes for the previous three years, receiving a total of $5,800 in refunds. Another did the same and recovered just over $10,000.
In earlier newsletters, I shared Wendell’s story from North Carolina, where he received over $30,000 back from the IRS. The list of success stories is endless, with many of them featured as live, unedited video interviews on the Home Business Tax Secrets website or in the Facebook group.
Turning Social Media Posts Into a Book
A Purpose Born During the Pandemic
In March 2020, when the pandemic forced us all to stay home, I found myself with extra time on my hands. I turned my attention to my Facebook group Home Business Tax Secrets, and began writing long-form posts to address the most common questions:
- How do I maximize my write-offs?
- What does “audit-proof” really mean?
- How do I organize everything without losing my mind?
That’s when inspiration struck: What if I expanded on these topics and turned them into chapters for a book? The idea of writing a published book began to take shape.
I had been educating home-based entrepreneurs for years, and the thought of curating everything into a comprehensive book felt like a natural next step. Over the next five months, I continued writing and immersed myself in learning about the self-publishing industry.
In August 2020, I published the first edition of The Home-Based Business Guide to Write Off Almost Anything!
The response from the community was incredible. By November, the book had become a #1 bestseller on Amazon in both the U.S. and Canada.
Building on the Books Success
The success of my book opened many doors. I was invited to be interviewed on numerous podcasts to share the message of tax write-offs for home-based businesses and my entrepreneurial journey. These stories also appeared in online articles, newspapers, and magazines, further amplifying the impact.
Reader Feedback Shaped the Second Edition
The success of my book opened many doors. I was invited to be interviewed on numerous podcasts to share the message of tax write-offs for home-based businesses and my entrepreneurial journey. These stories also appeared in online articles, newspapers, and magazines, further amplifying the impact.
By late 2022, after reading reviews and hearing feedback from readers, I realized there was still so much more I could have included in the first edition. I also had a growing list of tax strategies I wished I’d covered—such as addressing the needs of gig economy workers, rental income earners, navigating tax audits, setting up legal structures, insurance considerations, and more.
Determined to make the book even more valuable, I went back to work and started writing. In 2023, I published the Updated and Expanded Second Edition, and once again, the response was incredible.
The second edition quickly climbed to the top of Amazon’s bestseller lists and still frequently ranks #1 in the Small Business Taxes category. The book’s ongoing success has reaffirmed why I began this journey: to equip home-based entrepreneurs with the tools they need to thrive.
A New Chapter: The Membership Community
A Need for Ongoing Support
By 2024, I faced a pressing question: how could I serve more home-based entrepreneurs without overextending myself? My current offerings weren’t scalable, creating challenges both for me as an entrepreneur and for my clients.
While I wasn’t interested in creating a high-ticket course program, I knew from years of experience that my past course clients needed more than just “a course and a few hours of coaching.” They required ongoing support, up-to-date advice, and a space to ask questions as new challenges arose.
Then, while listening to an episode of the Side Hustle podcast, I had a lightbulb moment. The host posed a pivotal question: “Do your people need a one-time course solution or ongoing support?”
For me, the answer was obvious. Everything I was already doing within the Tax Write-Offs Made Simple System pointed to the need for ongoing support. At last, I could see the solution.
Creating the Membership Community
I immersed myself in learning everything I could about building a membership community that would revolutionize my offerings and meet the evolving needs of the home-based business community.
The result was clear: a membership model was the solution my audience needed—and it was the missing piece for me as an entrepreneur serving this community.
I dove deep into research, listening to podcasts like Flipped Lifestyle, and even joined their membership to access their blueprint and community insights.
In late 2024, I launched the Home Business Tax Secrets Membership Community, built on seven key pillars:
- Tax Write-Offs Made Simple System: Full access to the online course, a comprehensive workbook, and templates to help members stay organized and compliant.
- Live Tax Clinics: Monthly Q&A sessions offering expert, real-time advice tailored to members’ unique situations.
- Support Materials: Expanded resources, including a newly updated 63-page workbook.
- Community Support: A space for entrepreneurs to connect, share ideas, and learn from one another.
- Special Workshops & Business Trainings: Monthly live workshops on sales, marketing, time management, budgeting, and more to help grow your business.
- Coaching Plus Office Hours (Membership Plus): Book 45-minute one-on-one sessions with me for personalized tax, write-off, or business advice.
- Personalized Email Support (Membership Plus): Get direct email access to me for quick, tailored answers to your tax or business questions.
- Pre-Tax Season Filing Review (Membership Plus): I’ll review your records to ensure all deductions are claimed and your filing is audit-proof.
Empowering Entrepreneurs Year-Round
This membership provides home-based entrepreneurs with the tools to confidently claim tax write-offs, become audit-proof, and build financial confidence—all at a fraction of the cost of the standalone online course. More than a program, it’s an ongoing partnership designed to help entrepreneurs succeed.
Finding Confidence Through Support - Alysa's Story
Alysa Golden, a home-based entrepreneur from Toronto, has been featured in previous newsletters and on my website for her inspiring testimonial about my online course and coaching.
Alysa joined the Membership as soon as it launched, saying, “I always felt like I was missing something. Even though I had some success, I still didn’t have the confidence to do it myself.”
Like many entrepreneurs, she avoided addressing this part of her business, letting receipts pile up and fearing she’d make a mistake. For Alysa, it wasn’t just about taxes—it was about overcoming the mental block that kept her stuck.
Through the Membership Community, Alysa is building the confidence she needed. “Doug made it so approachable,” she shared. “He didn’t just give me the tools—I finally felt like I could actually do this.”
Alysa’s journey is exactly why I created this Membership: to empower entrepreneurs, provide support, and help them achieve lasting success.
Life Lessons: Embracing the Journey
If there’s one thing my entrepreneurial path has taught me, it’s that success isn’t a straight line—it’s a series of pivots, challenges, and breakthroughs. From overcoming financial setbacks to discovering the power of tax strategies, I’ve learned that every obstacle is an opportunity to grow stronger and wiser.
For home-based entrepreneurs like you, the journey may sometimes feel overwhelming, but with the right tools, guidance, and community, you can achieve clarity, confidence, and lasting success.
Take the Next Step
Imagine feeling confident, organized, and stress-free when tax season rolls around. The Home Business Tax Secrets Membership provides everything you need to make that a reality—from tools and expert advice to a supportive community of like-minded entrepreneurs.
P.S. Don’t let another deduction slip through the cracks. For less than the cost of missing one write-off, you’ll gain year-round support, actionable tools, and peace of mind tailored to your unique business needs. Join today and start saving!
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