Tom's woodworking journey so far can be split across three phases, the first of which starts in his childhood with both his builder grandfathers. The next phase began in circa 2015, after his time at Microsoft, when he developed an appreciation for woodworking during an apprenticeship in Baltimore. And finally, now, the third phase: an intensive woodworking course at the prestigious Krenov School in California. Tom describes still being at an 'infancy' stage where almost every design problem is still a 'first' for him, and the resulting joy and space that brings.
Prior to this, Tom was a veteran of Silicon Valley, having worked at companies like Twitter and Voyage. Today, he lives in a tiny home of 250 square feet with a 'Walden pond' vibe. We connected over Twitter when I came across a table that Tom and his shopmate, Hayden, had challenged themselves to build.
The question: how could they make a living building furniture in a sustainable way, whilst simultaneously respecting Krenov's tenets of care and craftsmanship?
In our chat, we talk about the four 'S' criteria (solid, small, simple and sweet), going back to school, 'woodworking mode' vs 'software mode', and creating impact through furniture.
I would love to start off by talking about your woodworking journey. I know that you're enrolled at a woodworking school—so tell me more about that.
Right now I'm a full-time student at The Krenov School of fine woodworking. It's up on the California Pacific coast. The program is very small and selective. I think a lot of people would argue it's one of the best woodworking programs in the world. It was started by a guy named James Krenov about 35 years ago.
We've got 12 students from all around the world, and we meet officially Monday through Saturday, 8:00 AM to 5:00 PM. So, six days a week, full time. And then most of us are here before and after that, as well on Sundays, based on what project we’re working on and deadlines and things like that.
It’s very much analogous to someone doing an immersion style of language learning—dropping in full time and trying to get better at something we enjoy doing. The program specifically is unique in its emphasis on hand tools and traditional joinery—a lot of woodworking curricula that are available today tend to err more towards modern machinery, CNC and things like that.
Wow. That sounds really fascinating. When did you start this course, and how long does it last?
I left my last position at Twitter in July of last year—then school started in the middle of August. I'm actually living in a neat little tiny home on my landlord's property, down in Mendocino. It’s super peaceful. I think the intention is to immerse yourself [in the course]. The course itself is a year long—there's an optional second year that some students choose to take as more of an independent self-guided study. My personal intent is to do this for the standard one year.
Did you have any training in woodworking prior to enrolling in the Krenov school? Where were you learning these woodworking techniques before?
My woodworking journey has three phases to it. The first one was when I was a young kid—both of my grandfathers were builders. One was a professional machinist and the other one was a really involved hobbyist woodworker who had his own wood shop and things like that. One of the things I regret is not taking advantage of that more.
I get to go home now and see these beautiful handmade tools or toys that my grandfather made for Christmases and birthdays, and I have a much different appreciation for that now—because when I was a little kid, computers were my first fascination. And so while my grandfathers were definitely excited and available to show me what was going on in the shop, my curiosity was predominantly in computers and programming and building websites and things like that—building in a digital sense.
Oh wow. What was the second phase?
The second phase—and where I really started to get an appreciation for woodworking—was in the 2015/2016 timeframe. I left a job at Microsoft and I had sold a software company that I had started a couple of years before that. I ended up on the east coast, and when we moved we didn't bring any furniture with us. So I entered woodworking as a potential buyer.
I found a local maker in Baltimore, Maryland, who had this beautiful Etsy shop and he made really cool, mid-century modern type pieces. I found out his shop was only about a mile from where we were staying, so I went by with the intention of getting a quote on a bed. At the time the bed was far too expensive but I hit it off with the guy who owned the shop. I could tell that he was really busy—all the benches and storage areas in his shop were taken up with active, cool-looking projects. I had left my software job and was taking a little time off and was like, “Hey, I'd love to learn how to do this.” He basically said, “show up tomorrow.”
We ended up formalising an apprenticeship arrangement where I worked for him for free for a couple of days a week—and then in return, in addition to the instruction, he gave me free access to the shop and my own bench space and things like that for me to design and build my own pieces of furniture.
I had a little under two years of experience working in that shop in Baltimore, both building the pieces that he was building for clients, but also designing and building my own things. I was fortunate to have a couple of friends, and then professional acquaintances, who commissioned some custom bed frames and smaller pieces of furniture. That was where I seriously discovered woodworking.
What did you enjoy so much about that apprenticeship?
I’ve been fortunate to work in some really cool technology startup settings and at some pretty big technology companies—and there's definitely a fulfilment working on a piece of software that touches millions or billions of people on a daily basis—but there was something really cool about woodworking. I found the feedback cycle to be really intimate and immediate.
If I'm at Twitter, for instance, designing a feature, the time between me working with my team to propose something and then getting engineering estimates, and then waiting for it to get built, and then working with people that test it, and then rolling it out to a small number of people—the time between idea to it actually being in people's hands is quite long, which is a little counterintuitive.
What was your journey from that apprenticeship to The Krenov School?
I had had a couple of life changes that brought me back out to Silicon Valley and back out into some of these traditional tech jobs—but I always had this itch in the back of my mind of, ‘What would it be like to really try to go in and learn this craft full time?’
With the pandemic and a bunch of changes to how things were with remote work, I had an opportunity to come up and see some student work at the program here. I drove up one weekend in February of 2020 to see the student showcase and it was just—I walked in and I was amazed.
COVID threw a bunch of wrenches in the process, but I ended up finally getting a spot at the school and having the opportunity to start last August. That’s been the third chapter—really opening myself up to it and doing it full time. It's more than a full-time job, honestly.
Before you decided to enrol, did you spend a long time researching and deciding if you were sure about the change?
It was interesting because there was a process to try to do it responsibly. But there was also this moment of intuition. I went into this student showcase and I can remember the first three cabinets that I saw when I walked into the gallery. I was just so impressed by the level of craftsmanship and design and execution. I was thinking, ‘This is what can happen. I can be one of these people if I take the chance and dedicate myself to it and this immersive approach.’
What's a day like for you now?
There’s not a whole lot going on outside of the coastline. It's a very small town. My daily routine is very different from what it was at Twitter or any of the other startups.
I’m usually up around 6:30 AM in the morning. I make coffee in my tiny home and some breakfast and then have about a 15-minute commute up to school. Once I'm here at school, it's woodworking mode.
When we're here, the vast majority of the time is working on a focused portfolio piece each semester. In conjunction with the professors, you try to push yourself. It should be a piece that isn't something that you can finish in a week or two intentionally—we're trying to scope a piece that is going to take us the significant part of the semester and try to push us in a direction that stretches us as a craftsperson.
How is a school day structured?
There is a curriculum and three or four times a week we have an hour or two of lectures from one of the professors. That can be some combination of academic historical context or it can be super applied, where they're showing you a particular joint or technique and taking you into the wood shop.
There is this really cool separation of practices at the school. One half of the building is the machine room, which looks similar to most modern furniture maker’s shops, but then the school has been very intentional to keep half of the building to just the hand tool and bench room.
So each student has their dedicated bench, and there's a place to keep all of your hand tools, including the ones that you build as part of the curriculum. There’s this quiet, almost meditative space to do the elements of difficult joinery and the hand touching and finishing that separates the type of work that we try to do here versus somebody who's building 200 cabinets a year and everything is automated and mechanical.
I was on The Krenov School’s website and I saw a piece that you did called Morning Routine. Is that one of the portfolio pieces the one that you mentioned?
Yeah. That was my first semester project. The first semester is a little bit different because they put you through this boot camp of core woodworking skills the first two months that you're here. Building your hand planes, dimensioning and finishing wood and learning different types of traditional joinery, like mortise and tenon and dovetails.
There’s a very high bar to get through that—it's very common, for instance, for people to start cutting dovetails and have to do it 5, 10, 15 times before it’sat a level that we'd like to encourage and expect at the school.
Whilst that sounds intense, the spirit of it is to try to get really good at doing important parts of woodworking, so there’s a lot of encouragement from the professors.
After that, you have the rest of the semester to build your first piece—so they intentionally try to guide you towards building something that is smaller in scope and scale in that first semester, because you've used up a good chunk of the semester on the core curriculum.
The guidance is actually that the project has to meet the four ‘S’ criteria.
You have to use actual solid wood, and not anything vineyard or composite or manufactured.
Small is the second—it should be something vaguely that you can put your arms around you and hug in terms of size. It shouldn’t be massively large.
Simple is the third criteria. Whilst they want you to be intentional about stretching yourself and incorporating a new skill or technique, they also want it to be achievable so that you can get it done in time.
Then the fourth one is the most subjective, which is sweet. The best definition of sweet that I've heard about is incorporating some level of enjoyment and appreciation for the user within the furniture.
Those are the four tenets of the first project—and so my project for that was Morning Routine, which was a cabinet built around my daily coffee routine, and would be able to hold the type of things that I use on a daily basis to make coffee.
Beautiful. Where is the piece now? Is it in your home?
So, each semester wraps up with a gallery show, and it's usually at a local gallery up here on the coast. We all have the opportunity to go through the process of installing our piece, writing a description and putting it up for sale if we want to. I decided, as someone who's looking at trying to do this full-time professionally, to place the piece for sale.
It actually sold about a day and a half into the gallery show, and it was by far my biggest ticket item that I've ever sold as a furniture maker.
That's really lovely. How does it feel being back in school?
That’s a great question. Honestly, it's stirred up a set of anxieties that I hadn't felt in quite a while. What's interesting is I've been really fortunate to work with some awesome teams and for some awesome companies in the software world for a long time—a decade plus—and you develop some confidence and some sense of what, hopefully, you contribute to the team and the company, and where your strengths and weaknesses are.
Going back to school after so long has definitely shaken my frame of reference. You have this thing where, yes, I've done some woodworking before, but this is an entirely different level of craftsmanship and technique and expectations. You do feel that stereotypical first day of school feeling—you have no idea what it's going to be like. It's everything from the actual academic side of things—”Can I do this?”—but there's also the social elements too. People from all over the world apply to the school and have different sorts of backgrounds and motivations. So you're meeting people that are very different from the folks that you worked with for the last decade in Silicon Valley.
But, my worst case day right now is, I wake up next to a beautiful coastline and maybe I cut some bad dovetails—and it's this very hands-on learning opportunity where I know I can always cut another piece of wood and try to try to get a little better. It’s very much this idea of searching for progress day after day.
For me, I think that's a lot more enjoyable or in line with my personality than going back to a PhD program in computer science or something like that.
Earlier, you mentioned that you go into ‘woodworking mode’. How does ‘woodworking mode’ differ from ‘software mode’, back when you worked in software?
That’s a great comparison. It's very different. In woodworking mode, I actually spend probably about 90% of my time in the quiet, hand tool part of the building that I was talking about.
I always have a cup of coffee by my side, my phone is off—or it's run out of battery and I haven't noticed. I'm not online when I'm in school. I'm not plugged into Twitter or Instagram—I'm working on the project at hand. During the drive in the morning, I spend a lot of time thinking about what problem I can tackle today.
It's at this really interesting infancy stage right now where I haven't been doing this level of woodworking long enough to have solved the majority of problems. When I run into a new issue or a new design challenge, it's often the first time I've ever tried to do something like that—so you have this interesting exposure to seeing problems for the first time, and that's very different from in software. [In software] you have these patterns that you've recognised and, in woodworking, your question is much more of this ebb and flow, meditative, try-something, throw-it-away, try-something, iterative type of thing.
It’s really cool to have a space where you can afford to be more thoughtful and intentional about each of these little steps and not just having to hit some specific deadline or roadmap.
Wow. You mentioned woodworking being meditative—do you consider it part of your self-care?
It definitely is. To share something about myself, since I've been up at school, I’ve actually celebrated a three-year sobriety milestone for myself.
Wow, congratulations.
Thank you. That has been a big life change for me.
Some of the culture and lifestyle expectations of being at big, high-pressure Silicon Valley companies introduced patterns that weren't the best for me. Part of coming up the coast to this beautiful coastline and to this awesome, amazing school is trying to explore a little bit more broadly, and discover what it means to be doing something that's sustainable. I think I'll have to go through a bit of a Goldilocks process here because this is the polar opposite of working in Silicon Valley.
One of the challenges of the program here historically has been attempting to find that Goldilocks zone right in the middle. It's very difficult to make a living building furniture the way that we're taught there. I build two pieces of furniture a year—and even if I can sell that thing as a piece of art for $10,000, it's difficult to make a living doing that.
And so, I did this exercise where I built a table. It was this attempt to start exploring what life could look like, more sustainably, when this program wraps up for me. I may not be able to dedicate six months for every custom piece of furniture that I make, initially—so how can I still make something that takes a lot of the tenets of care and craftsmanship and thoughtfulness that we learned here and start thinking about doing it in a way that allows us to make a living and be able to do this full-time.
So I made that table with a classmate of mine, and we haven't actually launched this yet, but we are thinking in the next week or so of announcing that we're going to be starting to put those tables into production under a new brand that we're starting called Edison Furniture.
Editor’s note: Edison Furniture has now launched.
Lovely. Am I right in saying that you intend to dedicate yourself to woodworking full-time after finishing at The Krenov School?
That is the goal. The pragmatist in me from years in software and computer science and that type of culture is thinking about it as if we were releasing a new feature at a software company—why customers might like a particular feature, ways of measuring whether that was the case or not, or if they're coming back and using the service more often.
We want to be making really wonderful, beautiful, thoughtful things that lots of people can appreciate in their homes—there's no magic playbook for that. At least that I'm aware of. And so some of it is going to be taking that experimentation of building software products and trying to apply it to this new domain.
Fascinating. Segueing into your previous life in product and software, you mentioned early on in our conversation that computers were your first fascination. Tell me about your journey towards computer science and software.
I remember that in our neighbourhood, at least, we were a little bit late to the internet—AOL instant messenger, that type of thing. When we got it, I got sucked in.
I remember thinking initially how cool it was that the internet was something that anybody could contribute to. At the time I was a 12 or 14-year-old kid, so I certainly thought that my journal posts were more important than they were in actuality.
I got lucky—a lot of people's first job is working in a restaurant or retail or mowing lawns—but my dad had a friend who had this manufacturing consulting business and he was looking for somebody to build a new website for them, so it gave me an opportunity at 16 years old to do that.
I knew nothing about HTML and CSS and JavaScript and cross-browser compatibility and all this stuff—and, mind you, this is in the days when lnternet Explorer was still a thing and brutally inconsistent with every other browser—but he gave me free reign to learn on the job since it was a skill set that they didn't have in house. My compensation for that project was my first car—so I had this really strong association with building for web and software and product as having this very meaningful, direct impact on my life.
That’s amazing. What about heading into university?
In the Northeast it was not common to have a computer science curriculum, so everything going into university was self-taught, and largely in the web domain.
What university did for me in the computer science program was give me an understanding of the creative power of software—and when I started getting a taste of real computer science and data structures and algorithms and scale, that was addictive to me.
Another fortunate right-place, right-time part of my career was, as I was a junior in university, a little thing called the iPhone came about—and in the summer between my junior and senior year Apple released the iPhone 3. It was the first time that they were going to let third-party developers build apps for the iPhone. It's crazy to think about that. The word app was not in the common vernacular—nobody knew what an app was because nobody had a smartphone—but it was this super new, cutting edge thing.
I was able to get an office at university from one of the professors who liked us for the summer, and so we had our own little startup office. We built an app for one of the public transit systems in the Bay Area called the BART System—and we had no idea what we were doing. It was horribly marketed. We called it iBart, like the Apple name thing—it’s just brutal. But we were one of the first few hundred apps to ever exist in the App Store. And that was such a catalyst that the app really took off.
And so I did a nine month stint at Microsoft out of school when my business partner was a year behind me, and then we decided that we were going to try to go the big Silicon Valley route and get some funding. We got into Y Combinator, and I left my job and moved down and we started doing that for a couple of years. It ended up getting way bigger than we ever thought it could. We ended up selling that company to Apple in 2013, and interestingly the outcome was that it afforded me the financial flexibility to take an unpaid apprenticeship in a wood shop in Baltimore and get exposed to woodworking.
One of the things I'm grateful for as far as this woodworking adventure right now is that I’m working with a really cool education startup in the Bay Area as an advisor—so I get to consult for a few hours a week and still scratch that software itch.
Do you miss being full-time in product or in software development since it was your first love?
That’s a really good question. Obviously, I made way more money working as a product manager than I probably will ever make woodworking, and that’s a reality that I've been working on coming to peace with because it is a huge lifestyle change.
It really does impact everything else that you might want to do and where you want to live and if you want to travel. What I would say is a lot of the creativity that I enjoyed in building software and product is really well satisfied by my experience with woodworking so far.
The biggest difference, as we talked about with Edison, is the scale of impact. I think it's really cool to build a chair or a dining table that is a centrepiece of somebody's home for decades—hopefully multiple generations. I remember my first mentor in Baltimore talking about how he enjoyed building dining tables specifically because he said that's where life happens. It's a really cool way to leave your fingerprint on somebody's home.
One of the interesting things that Edison Furniture starts getting at is that itch for scale as well—trying to find that happy medium. Twitter has hundreds of millions of people who use Twitter every day, so when I released a software product at Twitter, that was the scale of the impact. It's very unlikely I'm ever going to build 200 million tables. My hypothesis is that there's this happy middle ground where I can take a lot of the intention and care and design that we learned here at the Krenov School and make it something that is accessible to way more people. It's not just buying a single piece of art that one person in the world has—but instead, hopefully hundreds and thousands of people have this piece of furniture that plays this really cool role in their home and their lives.
Why the name Edison?
It speaks to this notion of invention and experimentation. Obviously, Edison is famous for the light bulb and a whole bunch of different inventions and patents and things like that. If you read about him, he’s also equally famous for all the things that didn't work—all the attempts of welding, all the prototypes that never made it to becoming world-changing inventions.
You’ve definitely always loved creating things. What are some of your other passions and creative outlets?
I also play music. It’s one of the things that I'm most insecure, and least confident about. It has always filled this role in my life of being something that didn't have to be performance-oriented. It’s always been self-taught—very much a YouTube, self-directed learner type of thing.
As I've gotten into that hobby, some of the builder in me starts to come out as well. So, I’ve also gone through the process of building my own tube amplifier and doing guitar mods and little guitar pedal kits.
I’ve also seriously considered attempting to start on an archtop guitar for the semester but decided that might be a little too ambitious for me out of the gate.
The other thing that has popped up that was unexpected, I don't know if we can call this a creative outlet, but I really enjoy coaching youth baseball. I talked about how I would like to label myself a builder and an engineer and certainly enjoy that work—but one of the unexpected benefits of having these management roles over the last few years has been the team-building element of it, and helping people to develop and grow and trying to build a team that's healthy and has diverse perspectives.
There's a ton of overlap between coaching baseball and building teams that work well together. Whilst I would have never independently expected to get a lot of fulfilment out of that aspect of the job, it's been something that I've really enjoyed—and I hope that no matter where the furniture woodworking goes if we're fortunate enough to be able to start and grow a business and build out a team, that some of those things will carry over.
Absolutely. I have two parts to this question: are you a perfectionist, and do you have to be a perfectionist?
That’s a great question. I’ve identified as [a perfectionist] for most of my life, and it can be difficult to deal with. On paper, I had a lot of accomplishments—I was valedictorian in high school and valedictorian finalist at university and captain of this team and that team and had a company sold to Apple—all that stuff on paper looks really cool, and I'm grateful for it, but what I've been really reckoning with over the last couple of years is whether that’s healthy, sustainable, or even desirable.
I’m definitely in the middle of trying to figure that out. Even in that core curriculum for The Krenov School that I mentioned earlier, I think I finished dead last in terms of finishing time. When I saw the requirement to have a perfect dovetail or a perfect joint, I was going to the nth degree of trying to make sure that it was okay.
One of the things that has been really good for me is that wood has its own personality and its own medium—it's gonna move and shake, and even if for one second I could get this piece of board that has a perfect angle and perfect flatness, the reality is that we're trying to build something that people are going to use. That coffee cabinet is going to get opened and shut 10 million times, I hope. That means that those things are gonna move and they're going to get scratches and they're going to get bumps and dents. But that's going to be part of what makes it maybe more perfect or more beautiful: they're the evidence that people are using it.
One of the big takeaways of my time here has been not trying to overcome perfectionism, but being open to the idea of, “What does good or perfect mean?”—maybe having a little more open-mindedness about what that is.
I love that. A lot of your opportunities so far seem to have been very serendipitous. Luck, opportunity, talent—where do all of these fit into your life?
I’ve battled with this, too. This is a conversation that comes up a lot in tech about imposter syndrome. We have these really awesome, talented, bright people who always have this voice in the back of their minds saying, ‘Man, if only the executives can wait one more week before they find out that I'm not good enough to do this job.’ Objectively, from the outside, you look at these awesome people and know that's not the case at all.
Chris Sacca, who's a big investor in Silicon Valley, tweeted something that really stuck with me—he said, it might be luck, but it's not an accident.
There have been some really fortunate things that have happened—we built one of the first few hundred apps, and that's become this tidal wave of influence, we were just in the right place at the right time—but at the same time, that would have never happened if we hadn't busted our butts and got into that university program to meet that professor and becoming top-performing students to have the opportunity to have an office or the intuition to take a chance on this thing that looked technically promising or whatever it was.
I feel like that framework has also been relevant, candidly, to my sobriety journey as well. This idea that, if you put in the work day-to-day to get the specific outcome that you want, this stuff starts happening in your world that—it may feel lucky or fortunate—but it's actually the by-product of consistency and trying to put good energy out there and help other people in the world.
I read the book The Alchemist at the beginning of my sobriety journey, and there's a famous quote in there. It's something to the effect of, “When you set your path after the thing that you really want, the universe will conspire to assist you.”
When you go for this thing that you are really passionate about, and you put in the time and effort and energy and earnestness, you put yourself in a position to be successful. And that's how I've squared away the luck-talent-timing variable matrix.
