7: The Chad Gagnon Episode

In this episode of the Huge Transformations Podcast, hosts Gabe Torres interviews Chad Gagnon, the newly appointed CEO of Blue Skies Bookkeeping. Chad shares his backstory of starting out as a real estate photographer and working his way up to help scale a real estate marketing firm to over $20 million in revenue across 32 states. Chad breaks down the importance of transitioning from being “on the truck” (doing the technical work) to delegating effectively, building a strong client success framework, and focusing on high-level growth. Now at Blue Skies Bookkeeping, Chad’s vision is to create the industry’s go-to bookkeeping service for home service businesses and eventually land on the Inc. 5000 list. Whether you’re a small home service entrepreneur or a seasoned business owner, this episode offers practical advice on leadership, delegation, and systematic growth.

SHOW NOTES
Guest: Chad Gagnon – CEO of Blue Skies Bookkeeping

• Background:
  • Started as a real estate photographer
  • Helped scale a real estate marketing startup to over $20M in revenue
  • Passionate about client success, proactive problem-solving, and leadership
• Current Focus:
  • Leading Blue Skies Bookkeeping
  • Aiming to become the largest bookkeeping service in the home service industry

Key Topics

• Entrepreneurial Beginnings
  • From photography and floor-plan creation to managing enterprise-level real estate marketing
  • Lessons learned from rapid scaling and multi-state expansion
• Scaling Challenges
  • The fear of handing off tasks and trusting a team
  • Importance of proactive client success strategies for retaining major accounts
• Leadership & Delegation
  • Wearing multiple hats in early business stages
  • Knowing when and how to effectively delegate to focus on strategic growth
• Vision for Blue Skies Bookkeeping
  • Chad’s goal to make Blue Skies the top choice for home service bookkeeping
  • Plans to reach the Inc. 5000 list
• Four Critical Questions
  • What is working?
  • What is not working?
  • What does success look like?
  • What is my biggest concern?

Actionable Takeaways

• Delegate to Grow: Letting go of day-to-day tasks is essential to scale.
• Proactive Client Success: Don’t wait for complaints; solve potential problems early.
• Ask the Right Questions: Use Chad’s four questions to guide weekly, monthly, or quarterly reviews.
• Long-Term Vision: Keep your eyes on a bigger end goal (e.g., Inc. 5000) for sustained motivation.

Resources & Mentions

• Blue Skies Bookkeeping
• Inc. 5000 List
• Huge Convention (Aug 20–22, 2025 in Nashville)

Additional Resources

• Huge Insider Newsletter
• Huge Foundations Education Platform (120+ Hours of Specialized Business Training)
• Huge Mastermind (For $750K+ Revenue Businesses)

Enjoying the Podcast?

• Subscribe to the Huge Transformations Podcast
• Rate & Review on Apple Podcasts or Spotify
• Share with fellow entrepreneurs seeking to grow and scale

TRANSCRIPT
Gabe (Host):
All right, great. All right, so this is Gabe Torres here with the Huge Transformations Podcast. With us today we have Chad Gagnon, the new CEO of Blue Skies Bookkeeping. Welcome, Chad. Thanks for joining us.

Chad (Guest):
Thank you for having me, Gabe. I’m glad to be here.

Gabe (Host):
Absolutely. And where is “here” for you? Where are you at right now?

Chad (Guest):
Here is Denver, Colorado—gloomy Denver, which is rare.

Gabe (Host):
Actually it’s gloomy here too in Nashville. Cool. Well, we're excited to have you on board. You've done some stuff, and I’m genuinely excited to get to know more about you because I got a little tidbit at a lunch meeting we had a few weeks ago on some stuff you've done in the service space or just your entrepreneurial journey, and so I'm really excited because I think you've done a lot of stuff that a lot of people could learn from—actual tangible real experience, not theory or guru guesswork. So I think to kick it off, if you could just give everybody kind of a quick backstory on Chad.

Chad (Guest):
Of course. I think it's always important to start with where I'm from, my roots. Originally from Michigan, I went to school at Western Michigan University where I—that's where, I guess, my business background started, and live in Denver, Colorado via Miami, Florida. I was in Miami for about three years, working in a business that I ended up being with for about 17 years. So once I graduated from school, moved to Miami, worked for a small company for a period of time for about a year, and then hooked up with what at the time was a startup with a couple good friends of mine from college. The company was doing real estate marketing. So we were providing photography, floor plans, and 3D services for residential real estate for sale. And I hooked up with them when I was in Miami. The company at that time was very, very small, bootstrapped, very low revenue. We were just scraping by for a period, and I was actually a photographer myself.

Gabe (Host):
That was in Miami?

Chad (Guest):
Yes, that was in Miami.

Gabe (Host):
So when you said your business kind of started in Michigan at Western, was there something else you started doing there that got you interested in business?

Chad (Guest):
No, that was more just my education and kind of where it all started. I was just going to school there.

Gabe (Host):
Were you going to school for business?

Chad (Guest):
I actually was going to school for aviation.

Gabe (Host):
Oh, really?

Chad (Guest):
Yeah, so my background—major in aviation, minor in business. But you know, I'm in the home services industry now, so I think a lot of people, what they go to school for, they end up not doing—especially entrepreneurs. So it's interesting. But yeah, I went to school for aviation.

Gabe (Host):
Yeah, same. I went to school for diplomacy and world affairs, thought I was going to be an ambassador or something. Look what you're doing now. (Laughs) Anyway, cool. So you got to Miami and…

Chad (Guest):
Got to Miami, was doing the work myself—real estate marketing, photos, floor plans, 3D. I was going out to the homes, taking photos, creating floor plans, producing stuff for the realtor clients. That's a good point I want to make: I was actually doing the work myself, and a lot of people in home service, they know their trade well because they did it themselves. I think that's important to learn and understand your business. So I did that for a few years, and then one of the owners of the company and I—he was in South Florida with me—decided to move to Denver, Colorado, just because we wanted to live here. We were big skiers, wanted to be around the mountains and snow, so we decided to move from Miami to Denver. We didn't have an office or anything, working from home. Then I was able to, in Denver, slowly grow the business. We were very sales focused, very quality focused, very client focused. And with that being top of mind, we grew the business over a course of 17 years. We were very successful with it. We became the largest real estate—one of the largest real estate photography companies in the country, operating in about 32 states and all the major metropolitan areas in there. We were able to grow our contractor network of photographers to north of about 500.

Gabe (Host):
So you guys really did scale that company, then—you're in 32 markets and had that deep of a network. What was revenue looking like at that point?

Chad (Guest):
Revenue at the highest was probably around $20 million. We grew it pretty big. I mean, when I started, it was maybe under $100K. We grinded for a very long time, learned a lot.

Gabe (Host):
That's insane. For you, in that time, you said you wore a lot of hats. Were you ops, or growth?

Chad (Guest):
I wore them all. I'd say basically every hat. So I'd left Miami, no longer shooting photos, more ops. I'd handle production day to day—photos going from the photographer back to our clients. I'd oversee that, plus customer support, client success, eventually technology, marketing, sales, finance. Over time, I'd fill the seat that needed success. The reason for that was the company needed success in that seat at that time. I would do everything I could to make it happen.

Gabe (Host):
So you're a true entrepreneur. (Laughs) So what's your favorite hat?

Chad (Guest):
Client success. Many home service companies might not know the term, but it's a proactive approach to retention. We ended up dealing with what we called enterprise-level accounts, so we needed more than just a support line. We built a client success department—onboard clients, meet monthly/quarterly, have proactive conversations. If you add value, you get a client for life. So I had to create that department, and that's probably the coolest hat I wore.

Gabe (Host):
Yes, so true. We see that in my own business—like enterprise-level accounts want more than just a phone call if there's an issue. Very different approach. So let’s pivot: what's a big challenge you faced?

Chad (Guest):
Well, the big challenge is probably handing off tasks and trusting a team. If you're an artisan or you know your trade well, trusting someone else to do it is big. But once it happens, and it happens right, you can get off the truck or out of the field and focus on growth.

Gabe (Host):
Yes, that's huge. So let's go to tangible practices. I like to ask: any exercise or tool you used that was super impactful?

Chad (Guest):
I like to keep it simple. Four questions I always ask, whether daily, weekly, monthly, quarterly:

1. What is working? Lean into it, celebrate it.
2. What is not working? Make it visible, solve it.
3. What does success look like? Define it for the day, week, quarter, etc.
4. What is my biggest concern? Identify it, let the team help so you’re not the only one staying up at night.

Gabe (Host):
Yes, that's awesome. I'm going to do that right now in December. Perfect. Last question: you're now at Blue Skies Bookkeeping, not at the real estate marketing firm. Where do you see Blue Skies Bookkeeping in five years?

Chad (Guest):
In five years, I'd like us to be the largest bookkeeping service for home service companies, letting owners do what they're good at. I'd also love to see us on the Inc. 5000 list. That's the big end goal.

Gabe (Host):
Awesome, man. Thanks for taking the time. I know you're super busy.

Chad (Guest):
Absolutely. Thank you. It was great.

Gabe (Host):
Yeah, have a great rest of the week, Chad. I'll see you.

Sid (Host):
Hello, my friend, this is Sid. Thank you again so much for taking your time to listen to today's episode. I hope you got some value from it, and listen—anything that was covered, any of the resources, any of the books, any of the tools, anything like that is in the show notes, so it’s easy for you to find and check out. And also want to let you know: the mission for The Huge Convention and for this podcast is to help our blue-collar business owners—like you and me—gain financial and time freedom through running a better business. And we do that in four ways:

1. Our free weekly newsletter—it’s called The Huge Insider. Hope you subscribe. It's the most valuable newsletter for the home service industry, paid or otherwise, and this one’s free.
2. The Huge Foundations education platform—over 120 hours of industry-specific education and resources for you. Every month, we do a topical webinar and Q&A with seven- and eight-figure business owners, and it's available to you for a $1 trial for seven days.
3. Of course, The Huge Convention—if you haven't been, you got to check it out. It's every August, this year in Nashville, Tennessee, August 20th through 22nd in 2025, and it is the largest and number one rated trade show and convention for home service business builders. We've got the biggest trade show so you can check out all the coolest tools, meet the vendors, check out the software to run your business. We’ve got world-class education and educators and speakers that will teach you how to run a better business. And it's the best networking opportunity you can have in the home service business.
4. Lastly, if you want to pour jet fuel in your business, check out The Huge Mastermind. Now it's not for everyone; you got to be at over $750K of revenue, building toward $1M, $5M, or $10M in the next five years. It’s a network and a mentorship and a mastermind of your peers, and we help you understand and implement The Freedom Operating System.

We go into more detail, but you can get all the information on all four of these programs and how we'll help you advance your business quickly just by going to thehugeconvention.com and scrolling down and clicking on the Freedom Path. Or, of course, you can find the links here in the show notes. Sorry, I feel like I'm getting a little bit wordy, but I just want to let you know of the resources that are available to you to help you accelerate and advance your beautiful small business. So keep on growing, keep on learning, keep advancing. And if you like the show, go ahead—if you would go and take 90 seconds and give us a review on iTunes, then subscribe and share it. Man, it would really mean the world to us, it would help other people, and as we continue our mission to help people just like you and me. So thanks again for listening, we'll see you on the next episode.