A Conversation with a former Nuclear Submarine Officer...
...who's navigating a W2 executive role while also running a niche manufacturing business in the background
I’ve known Wes for a long time, and I’m proud to call him a friend. His story is one of those rare narrative arcs that captures almost every modern career archetype in a single life — father, husband, engineer, military officer, founder, executive, consultant, operator, and more recently, owner.
From suburban Philadelphia to Penn State to the U.S. Navy’s nuclear submarine program, his early career was defined by structure, discipline, and pressure only a select few can possibly imagine. From there he earned an MBA at MIT, then dove right back into choppy waters — this time entrepreneurship. First was a startup in the maritime space. He experienced failure early, taking away lessons that served him well not only in his reinvention within the worlds of management consulting and enterprise software, but also his next entrepreneurial adventure.
What makes his story stand out is how many chapters overlap rather than replace one another. Today, while serving as a senior executive in SaaS, he also owns a small manufacturing company in the background — a quiet, well-run, simple little business that provides both additional cash flow and the entrepreneurial experimentation for which so many yearn. Wes exudes a fascinating blend of the digital and the physical, of ambition and practicality — proof that life can be a “portfolio” of life experiences and overlapping business pursuits.
We hope you enjoy this one.
Wes, tell us about where you grew up and your early family life.
I grew up north of Philadelphia near Doylestown, went to public school there. I was privileged that I grew up in an affluent area with really good schools. My dad was in pharmaceuticals and travelled frequently up through middle school. His work ethic and motivations definitely rubbed off on me. I remember him telling me as a kid that the only way to really make “fuck you money” was to start your own business. Later in his career, he struggled with ageism and hit a glass ceiling. After spending so much time away from his family in the prime of our childhood, it felt like a really abrupt, thankless way to end his career.
So how did this influence your own life and career decisions? Walk us back.
I went to Penn State for mechanical engineering. I knew I didn’t want to really be an engineer and design parts all day, and always had interest in joining the military actually. At the time, Iraq and Afghanistan conflicts were in full swing. I wanted to join the Marines and do my part, but shopped around the services. The Navy offered to use my engineering education and to train me to operate nuclear submarines. It was a balance between the four years of investment I had put into my education, an adventure with real national security implications (subs do some really cool shit), and a way to differentiate myself coming out of the service.
I did my five and ultimately transitioned out after some really stressful years. I applied to top tier business schools and was accepted to MIT and Carnegie Mellon. My wife at the time was also accepted to a Boston based masters program, and we preferred Boston over Pittsburgh. Ultimately, MIT was the right next step and an excellent way for me to transition back to society and relearn to interact with people in socially acceptable ways.
I then started a technology business in the maritime shipping space with some other vets. It ultimately failed, but geez did I learn a lot. After graduating and a divorce, I did some serious self reflection. Professionally, if I ever wanted to do anything entrepreneurial again, I knew that I needed to learn sales. My first real job after school was a sales position for a local software company in Boston, that ultimately did really well. I learned a ton - lessons and tactics that I still implement daily 10 years later.
And now?
Now I’m the North American GM for a European technology company. And on the side, I own a small manufacturing company that my wife and I run in our free time.
So you’re still full steam ahead with your traditional career, yet were able to carve out enough bandwidth to buy a small business. You mentioned your father’s inspiration, but was there a certain moment when you decided to go for it?
Yes and I remember it well. I was the VP of Account Management for an Israeli software company. We were getting kicked in the face every day and a lot of our customers were churning. I owned the churn metric, and took a lot of the blame for the outpouring. A competitor of ours had just gone public and greatly accelerated their product to compete head to head with ours. They just had a better product. Saving our business account by account was incredibly taxing, unrewarding, and just flat out sucked. I knew I needed to do something different. Yes, thinking back to what my dad had taught me young - that wealth was generated by business owners - I started trying to figure out what that could mean.
Despite a business school education, I didn’t really know where to start, and wasn’t financially literate enough to know what a good SMB looked like. This was 2019 - search funds were just really becoming a thing and some material existed on that model. I read the HBR book and Buy Then Build - both incredibly helpful. I scoured BizBuySell, spoke to a handful of more experienced people that had done it as a late stage career move. I talked with brokers, a handful of owners, lenders - everybody that I could try to learn something from. Despite that, finding the right business eluded me, especially one that I felt like I could lever up and put essentially all of my net worth into the PG.
I remarried in 2018 and remember the conversation with my wife where I started making sense of my idea. We were hiking the White Mountains in New Hampshire. I was trying to process my dissatisfaction at work and figure out the path forward. Ultimately, I had the idea that I could maybe buy a couple small manufacturing businesses combine them into a larger entity. At the time, I was still too new to the M&A world to realize this was a ‘rollup’ strategy and that it was '“a thing.”
And she must have approved because you ended up buying one. What was the process like?
She was really the one who convinced me to buy it. Again, we had talked for years about me buying a business and quitting my day job, and about investing in higher risk, alternative assets that may generate larger returns for us down the road. Buying a “part time” business hit both of those buckets. It was a small niche manufacturer of industrial maintenance tools and components which was inherited by the daughter of the founder, who herself was looking to retire and put the business in good hands.
The numbers were strong, our diligence was little but enough to verify the financials, and the deal structure made it a no-brainer for us. The broker on the deal was actually a close friend from undergrad who first put the business on my radar. I trusted his judgement. I’ve found so many brokers to be somewhat sleezy and misrepresent numbers and health of the business in the interest of making a sale. It was tough to see through that noise. But buying through a friend made me trust the process a little more. And, the deal was small enough that if the business went to zero, we wouldn’t be bankrupt.
So now you’re both an executive and an entrepreneur. How does your family describe what you do? Do they get it right?
Great question. I intentionally try to keep my professional life separate. I’ve learned that I need space to disconnect otherwise I’ll be consumed by my own ambition. My kids are young, 5 and 6 months. I live in Boston and work my day job in NYC a couple days a week. My daughter knows I travel a lot and work hard. She also knows we have a small family business that sometimes steals me from her for an hour or two on weekends. She’s not old enough to get it yet, but hopefully she appreciates it when she realizes that our little family side hustle will one day put her through college.
On Identity and Lifestyle…
So then how has your own sense of identity shifted, if at all?
Another great question. I identified as a Submarine officer for a long time after the military. It took me almost 10 years to forgo that as my identity. It was a long path. As such, I had always felt a little like an outsider in the corporate world.
I closed on the business maybe 3 months after I had actually accepted a job at a major technology firm — the dead opposite of SMB ownership. Although there was nothing prohibiting me from a side hustle, it certainly wasn’t something I was going to advertise in that side of my professional life. To this day, I certainly don’t hide that I’m a business owner or try to keep it secret, but I also don’t openly talk about it in my professional software circles.
What have you sacrificed that you didn’t expect to in pursuit of your current path?
Sanity.
Going all the way back to my time in the Navy, I developed some really bad psychological habits. I was in a near constant state of ultra high stress aboard the sub. It changed my brain chemistry and wiring. After getting out, my stress levels went down, but my fight or flight response was still ultra sensitive. I remember when the first technology company that I worked at sold, I nearly had a panic attack. My overreaction to that was extreme. In hindsight, I was much later diagnosed with a complex case of PTSD. It took a long time to rewire my brain to think and respond differently to work related stress.
Since I’ve done that work, my balance is much improved. I still get stressed, but I don’t hold it as much. I have wellness and meditation routines that keep me level headed.
My day job now is a 5 hour commute when I’m needed down in New York, and I’m gone a couple nights a week. It’s a lot on my young family. My dad commuted to Connecticut and North Jersey for years when I was younger, and I saw the toll it took on him and my family. I vowed never to do that. And yet — here I am, doing exactly what I said I wouldn’t. The opportunity to lead in this capacity was just too much to turn down, and something I and my wife felt like I would regret if I didn’t take.
You’re balancing career ambition, entrepreneurial independence, and family life. It’s always a challenge, but talk about the latter. You’re a new father again. What do you and the family do for fun? To win back some sanity?
Kids change everything. My wife and I used to be super active and outdoorsy — hiking, climbing, skiing. We travelled internationally a lot. Now with young kids, all those things are much more difficult. My daughter is just hitting the age where she’s strong enough to do some real hikes. We were able to get a couple in this summer with her and the newborn. Ultimately though, any quality time with the family is good time. But it definitely looks different than it did six years ago.
Still, I was fortunate enough to take some serious time off for paternity leave. My wife and I overlapped our parental leaves for about 5 months over the summer. Tough to travel with a newborn so we largely stayed at home, but it was some of the best time I’ve ever had. I was able to connect with my kids, and mentally and physically reset myself from 15 years worth of trauma in my professional life. We took the kids to Disney in August which was easily the best family time we’ve ever had together. And we’re planning a Caribbean trip in January. I’ve found that getting out of New England and finding some sun has become medically necessary.
On Ownership and Career Realities…
This is a heavy topic and you’re probably the best person to opine on it. What are your thoughts broadly on the “W2 versus SMB” debate?
Lets start W2. People claim they’re safer and more secure. They’re not. I’ve lived in fear of being fired for most of my professional life. Just yesterday a former colleague of mine - now a C-level executive - was unceremoniously fired because of internal office politics. At my former tech company, we laid off 50,000 people over the four years I was there. There is no such thing as job security unless you own it.
On the SMB ownership, its WAY more complex than the podcasts, influencers, authors, and general ETA community would have you believe. Don’t get me wrong, it can all be learned, but there’s a steep learning curve. I hold a top-10 MBA, have run 350-person organizations generating $250M in revenue. Doing that has given me a huge leg up in understanding people management, strategy, etc. BUT, learning M&A and financial literacy was a completely different skillset. Even now that I own a small business, the complexities of accounting and financial statements often take much longer for me to digest than I would care to admit.
In this business, I also have to stretch technically. I’m a mechanical engineer by training so am able to get into the weeds a bit with my customers in heavy industrial companies. BUT, I’m not really an engineer. I can’t redesign our products or their components by myself. The plan was for my wife to help me run the business, but she self admittedly doesn’t have enough of a business or engineering skillset to really take much off my plate yet.
We’ve had other friends tell us they want to buy an SMB, get out of corporate, etc. We encourage them, but kind of smile and nod. This is not the path for everyone. It sounds great — and for us it’s worked out really well — but it requires you to learn a LOT more than most people want to, or may be capable of doing.
We can’t avoid risk on either path. But what about the rewards that accompany that risk?
In my day job, I’m a high earner and broadening my management skillset on someone else’s balance sheet. I would not be near the SMB operator that I am without some deep sales experience, and the opportunity to build and lead large teams. I know how to think strategically, how to hire well more often than not, how to build org charts and complex deal structures. All of this, I learned on someone else’s dime.
On the SMB side, I put down $80,000 cash to buy a business with $160,000 of topline revenue and about $50,000 of SDE. I was conservative in my assessment of those numbers. Our SDE each of the three years we’ve owned it so far has been north of $80,000. All in, I probably spend two hours a week on the business. They’re the highest paid two hours of my career. The net tax benefits of owning a business can’t be overstated either. I run the usual things through the business — phone, internet, car - which has really added up. A few hours a week has changed the financial trajectory of our lives.
Plus, because of both sides of my professional life, I’m far more comfortable now assessing what makes a good business, and would be way more confident buying something that requires a PG and would replace my income. I’ve learned some of the accounting gotchas, and know enough about managing a larger, fully functional P&L to step into a new ownership experience and be confident that it wouldn’t be a disaster.
What’s the most ridiculous thing you’ve had to learn hands-on in buying and running the business?
Everyone who buys a legacy business always thinks “I’ll just plug some software into this thing and get all kinds of modern efficiencies!” I was caught in that trap too. Looking back on it now, it’s a ton of bullshit.
I’ve tried three different inventory management systems. None of them have been able to get my workflow correct. I’m still flying blind and don’t know how much of which parts I have on the shelf at my manufacturing facility in NJ. I’m reimplementing one right now with a freelancer that I hired from Pakistan in one final attempt to actually get the business into a meaningful software suite. I’m not optimistic it will work.
Software companies advertise that they’re purpose built for SMBs. If there are, and they’re affordable, they won’t be able to handle any complexity. For us, it’s the subcontracting use case, which is easy in theory, but somehow difficult to implement. If they can handle the complexity, they either charge an arm and a leg for the software license or the services to implement… or both. Those products are built for large enterprises. They don’t give a shit about your $10K recurring license. It may be business critical for you to get right, but your vendor doesn’t care when they have multi-million dollar contracts with the Fortune1000.
Is there a number or process that keeps you up at night?
Luckily the stakes for our acquisition were fairly low. Our business has a pretty normal seasonality to it that I didn’t fully appreciate in diligence. Our first two years, we stopped hearing from customers in maybe March, and essentially were dry until August. Turns out its a fairly normal and repeatable cycle. But at first, there was definitely an “oh shit, did I break it?” kind of feeling.
How do you know when it’s time to close up shop, or shut the laptop, and call it a day on everything you have going on?
When I’m home, its usually by 5:30 unless something really big is going down. I prioritize the few hours I get to spend with my kids and set some very strong boundaries. When the kids aren’t in the background, I’ll work until I begin to run out of gas. Today I was in the office by 7, on the train to come home at 6, and I’m jamming away on some work on the way back. All in all, I’m a hard worker, but not a workaholic. I know that I need balance and limits to keep myself functional — both at home and at work.
On Highs and Lows…
Was the diligence and closing process generally smooth since it was such a small business?
So, in diligence, we learned that one of the metal alloys to make a key component of one of our biggest products was no longer available. No foundry would make the material, certainly not on the small scale that we needed. We ultimately found a dealer in Ireland and ordered 10 years worth of it prior to close, on the sellers dime. I expected that we’d have to come up with an alternative much sooner than that, but we’re good for a while.
If you exited tomorrow, what part of the SMB journey so far would you miss most?
The customers. Our little business gets me to think in a slightly different vector that I do normally in my day job. My customers are blue collar, salt of the earth type, heavy industrial workers. They’re dead opposite of New York software execs that I work with. They challenge me to think and communicate differently, and stretch my technical understanding. It’s refreshing.
What’s the one thing from your career or ownership years that you hope people talk about long after you’re gone?
I pride myself on being a leader. In it’s simplest form, I believe that a leader’s job is to make people better. That’s it. That’s the job. It’s my skillset, and I’m proud of it. My biggest hope is that with all the work I put in and invest into people that work with me, they come out and say “man, I really learned a lot from him. I wouldn’t be where I am today without that leadership, position, experience, etc. and I attribute that growth to Wes.”
I’ve been incredibly fortunate in my career to work with some stellar people and build some really strong teams. After leaving my last job, I had probably 30 texts, emails, or LinkedIn messages from folks that worked with or for me at some point. Almost all of them expressed gratitude for how much they learned during my tenure.
That’s the professional legacy I want to leave.
On Inspiration and Leadership…
Does anyone in particular inspire you in business?
No. I have very few people that I admire in a professional setting. Nearly everyone in the generation above who has been ‘successful’ professionally seems to have made enormous family sacrifices to get there. I respect what they’ve accomplished professionally, but I don’t want to model my life after them specifically in order to reach the same end.
Do you think entrepreneurs are born or made? Can so-called “intrapreneurs” exist and apply those attributes to a larger or more structured organization?
Both. Entrepreneurship requires a willingness to learn and learn quickly, a will to win, and some level of risk tolerance. A lot of people have those traits naturally and, if they don’t but are really motivated, can learn those traits.
Intrapreneurs exist, yes. I was one at my last firm. It’s much harder to reinvent a company from within as mid or even senior level management. Organizational momentum is a thing. That being said, the skillsets between entrepreneurs and intrapreneurs are similar, but the intrapreneur also has to be a master politician — something I can do, but I hate playing politics.
What do you know now about leadership or management that you would have chuckled or shaken your head at before?
Man. A LOT.
I could spend an hour talking about leadership. It’s so simple to get right, and so seldom done well.
Leadership consists of three things:
Set a clear expectation of where you want to go.
Enable your people to get there. Create the processes, materials, etc.
Hold them accountable to your expectations or, if your expectation was off, go back to Step1.
That’s it. To do that successfully, you have to care about your people. Deeply and personally. You have to be invested in their success for their sake — not your own. You have to be able to objectively measure their performance against the standard, provide meaningful coaching and feedback in a respectful way, and set a culture where it’s okay to fail once, but unacceptable to fail repeatedly without changing the process.
It’s simple. Hard to do, I think, because most leaders lose sight of actually caring about their people.
On Tools, Tech, and Process
Do you think most tools or processes are overrated or underrated in business? Why?
Yes and no. Some are an absolute necessity to be competitive. ERP, CRM, marketing automation are all basic requirements. You don’t necessarily need every bell and whistle to be effective, but you need a consistent system of record for finance and sales to operate in.
I do think that the mainstream hype around generative and agentic AI is overrated. The vendors that can do it really well are making a huge impact for a small selection of very large clients, and being relatively quiet about it. All the chatter around how ChatGPT and similar tools will change the world is bullshit. It’s a better search engine. It gets everybody back a little time in their day depending how they use it — and very few people are using it well — and occasionally pops out a picture of a cat riding a surfboard while giving you the finger that everyone gets a good laugh from.
Eventually that tech will be applied to really interesting business use cases. But that has eluded the software industry so far.
On Career Paths and Alternatives…
Will you stay in the W-2 world? If so, is your approach and perspective changing? Or do you think this framing of one path versus the other to be overly simplistic?
I would take another W2 job after this one, but will be very selective. My goal is to save enough money from my day job to double down on my ownership pursuits. I have no interest in retiring, but I’d love to get to a point where I own a couple small businesses, all with independent operators, and can put in 20 hours or so a week while maintaining a decent income. To me, that’s the dream.
What would you have done differently in your career, knowing what you know now?
Nothing. I have no regrets about how my career has progressed. I’ve learned something valuable at every turn, and would not be where I am today if I didn’t have the experiences I did along the way. I’m incredibly grateful for the opportunities I’ve been given, the people I’ve met, and the battle scars I’ve earned along the way.
If you were to jump into another business or add-on, or pursue a different career altogether, what would it be?
I’m a little all over the place on this one. Businesses that I’ve looked at and like recently include cabinet manufacturer, countertop sales and manufacturing, and architectural woodwork.
I’m also pursuing a potential tuck-in for my current manufacturing operation.
I think I’ve learned — after more than a decade in software — that I like to build tangible things. Everything I listed above is a physical product. I think there’s something nostalgic there that clings to my engineering roots. They’re not always the best business — usually lack recurring revenue streams — but there’s craftsmanship and something to hold at the end of the day.
Would you want your kids to follow in your path?
Yes, I will absolutely guide my kids toward an entrepreneurial path.
On Health and Personal Habits…
You mentioned earlier you were super active and outdoorsy pre-kids. What do you do to stay healthy and active now?
I lift weights 3 to 4 days a week. I often schedule an hour during my work from home days to accommodate exercise and give my mind a mid day break. I sauna and cold plunge a couple days a week. I’m maniacal about my diet, and take a TON of supplements. I recently recovered from a 5 year journey with severe Lyme disease, where herbal treatment finally got me back to health. I still take about 15 pills a day.
I spend as much time outside as I possibly can, and try to get out for walks, hikes, bike rides with the family whenever we can.
Is your personal life better, worse, same, or just different since the combination of owning a small business and advancing in your software career?
My personal life is in great shape right now, but I think its independent from any of my career decisions. Ultimately, I’m happy with where I am. I’m satisfied in my W2, feel like I’m building something for myself and my kids with my SMB. I’m fulfilled and flourishing professionally, and that emotional state is having positive influence on my personal life, but it’s not the root cause of it.
What’s the mantra or phrase you repeat to yourself most often?
Slow is smooth. Smooth is fast.
On Money and Investing…
Are you investing outside your business or career? Stocks, private deals, etc.?
Yes. Levered ETFs, balanced with traditional index funds. We have some money in a fund with multi family real estate, and own a couple percentage points of our local rock climbing gym — maybe not my best investment financially, but was an excellent investment in our community.
Do you believe the best financial investment is in yourself? Or other people?
Depends on your skillset. If you’re smart, educated, motivated, then maybe you’re best to invest in yourself. But even the smartest person with the right experience and the best idea is not guaranteed success. Healthy investment should be balanced and spread out.
Do you believe you’ve sacrificed some financial or career upside in order to pursue this balance between W2 and SMB?
No, I think I’m financially peaking on my W2 side with way more to grow into on the SMB side.
On Culture, Media, Personality, and Stuff…
What are some cool or interesting products you bought recently? Tell us about your material life.
We invested in our backyard this summer. We put up a pergola with an outdoor sectional and a TV so we could spend more time outside. I installed a sauna and a cold plunge to invest in my wellness routine. Both have helped me manage stress levels and stay balanced.
I do like cars. I recently bought a Ford Bronco as my daily drive that I absolutely love. And I have a Porsche Boxster that I take out on the weekends.
What projects, hobbies, or passions outside of work do you make time for?
Personal exercise and wellness routines, plus dedicated family time, take up the vast majority of my free time these days.
Are you involved in your community — volunteerism, local groups, politics?
I would love to be, but haven’t prioritized it. Eventually, when life settles out a bit, I’d love to be more involved and maybe run for a local office.
On Happiness and Outlook…
What does “success” mean to you now?
Success to me will be when I have full control of my time. That will likely come when I can get out of a W2 dependency, keep fairly high earnings, and do so with a flexible schedule.
All told, are you happy?
This is the happiest I’ve ever been in my adult life. I have a beautiful family, a house and community that I love, and a multi-faceted professional life that keeps me learning and growing. I’m very lucky and am incredibly grateful.
Thanks for doing this, Wes.
Thank you. Good to look back.