We were lucky to catch up with Caleb Stumberg recently and have shared our conversation below.

Caleb, appreciate you joining us today. What was it like going from idea to execution? Can you share some of the backstory and some of the major steps or milestones?

When I think back on how Second Son Woodworks actually started, it really began in a very practical, almost unplanned way. I grew up in Helena, Montana, where working with my hands was just part of daily life—helping family and friends with home repairs, learning to use tools, and figuring things out as I went. I didn’t think of it as “woodworking” then; it was just problem-solving.

The real spark came when I was in college in Seattle. My roommates and I had moved into this old Queen Anne house, and we needed a dining table. Instead of buying one, we decided to build it ourselves. We scavenged some reclaimed lumber and, piece by piece, crafted a cottage-style table and benches that fit perfectly into our kitchen nook. I still remember finishing that table with orange oil and steel wool—it wasn’t just about the table anymore. That process lit something in me. I realized I wasn’t just building furniture, I was connecting with the material, the craft, and the idea of making something both useful and beautiful. The house itself has since been demolished, but that table—and the experience of building it—remains one of the most meaningful starting points in my journey.

That was the seed of Second Son Woodworks. In 2016, I officially started taking on small projects. At first it was through friends and word-of-mouth, but I also posted ads on Craigslist to reach new clients. Those early jobs taught me what it really takes to run a business: setting up a workspace, sourcing lumber, and figuring out how to price my time and materials—none of which came overnight. It was a lot of trial and error, but each project gave me more confidence that this wasn’t just a hobby.

When I graduated and moved back to Helena, I kept building, refining, and saying “yes” to custom projects that pushed me out of my comfort zone. By 2018, I decided to expand my reach by starting a YouTube channel. My first video was a simple rolling workbench build. I didn’t know much about filming or editing, but I knew that if I waited until everything was perfect, I’d never start. So I hit record, posted it, and kept going. Today, that decision has grown into a channel with over 600 videos, more than 4.8 million views, and 18,000 subscribers. It’s been incredible to connect with a community of people who love woodworking as much as I do—and I’d love for readers to check it out and support it!

Now, based in Santa Barbara, Second Son Woodworks has become something bigger than I imagined back in that little Queen Anne kitchen. I take on custom furniture projects, and recently I started a service that turns fallen or at-risk trees into heirloom furniture for clients. It’s deeply rewarding to give new life to a tree that meant something to someone, transforming it into a lasting piece for their home.

Looking back, the process wasn’t a single leap—it was a series of small steps, each building on the last. From needing a table, to posting my first Craigslist ad, to sharing projects on YouTube, to creating a sustainable business here in California. The key was simply starting, staying open to learning, and letting the craft guide me forward.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m Caleb Stumberg, the founder and craftsman behind Second Son Woodworks. I grew up in Helena, Montana, where I learned to use tools and fix things alongside family and friends. The pivotal moment came during my college years in Seattle when my roommates and I needed a dining table. Instead of buying one, we built it ourselves from reclaimed lumber. As we sanded and oiled that table, I realized how deeply I connected to woodworking. That experience inspired me to start Second Son Woodworks in 2016, and I’ve been building ever since.

Today, based in Santa Barbara, CA, I specialize in creating custom, one-of-a-kind furniture pieces tailored to each client. My work ranges from dining tables, desks, cabinets, boxes, and shelving to unique live-edge designs. One of the things that sets me apart is my tree-to-table service, where I mill fallen or at-risk trees on-site and transform them into heirloom furniture. These pieces often hold deep sentimental value for clients, as they carry the legacy of the tree and the land it came from. I also offer locally sourced live-edge slabs for sale.

What I’m most proud of is the combination of craftsmanship and sustainability that defines my work. I focus on sourcing local wood and salvaging materials that would otherwise go to waste, turning them into furniture that’s built to last generations. It’s furniture with a story—something you won’t find from mass-produced, online retailers.

In addition to building, I share my craft with a larger community through my YouTube channel, which now has over 600 videos, more than 4.8 million views, and 18,000 subscribers. It’s become a way to teach, inspire, and connect with others who love woodworking. I’d love for readers to check it out and support it!

At the heart of Second Son Woodworks is the belief that furniture should be both functional and meaningful. Whether I’m designing a custom dining table, transforming a fallen tree, or sharing a tutorial online, my goal is always the same: to create work that’s personal, lasting, and crafted with care.

Can you open up about how you funded your business?

Being a business owner doesn’t mean you make a lot of money and instead it means you often don’t pay yourself and instead put money back into the business. I know this isn’t the best thing longterm but I do think that in the beginning you have to be willing to sacrifice to get the business going. That is what I did. I used personal money and what I made from projects to buy more tools. I have spent a lot of money on tools and I know I will spend more in the future. That is just part of being a woodworker. But that being said, I have done my best to not go into debt buying these tool and I am so happy I haven’t. It has made me more agile as a business owner and able to pivot when unexpected things come up. Unexpected things will always happen and you need to be prepared.

We’d love to hear a story of resilience from your journey.

After almost 10 years of running a small business, I still make mistakes with quoting/estimating projects during the early conversations with clients. This has resulted in me losing money. It is so frustrating losing money, however, the as a small business owner you need to have the resilience to bite your tongue and not say anything about it to the client. Eat the lost costs and learn from your estimating mistake(s). The reputation of your business if far more valuable than the lost revenue from one project, or even several.

Contact Info:

• Website: https://www.secondsonwoodworks.com/
• Instagram: https://www.instagram.com/secondsonwoodworks/
• Facebook: https://www.facebook.com/secondsonwoodworks
• Linkedin: https://www.linkedin.com/in/caleb-stumberg-3a3b0659/
• Youtube: https://www.youtube.com/@SecondSonWoodworks