Should I buy a company after visiting Victoria, BC?
What started as a tiny trip to Victoria turned into a deeper question about capital, optionality, and how to buy time.
I took a ferry from Seattle to Victoria, and all I could think about on the way back was: Which company should I buy (not build) to generate free cash flow?
If you’re a seasoned software engineer in the age of AI who lives to build, you’re probably thinking how ridiculous this sounds.
Well, Andrew Wilkinson planted a tiny seed in my mind, and it has started germinating.
Strap in. This post is about making plans without expectations, how that mindset extends into everything else in life, and if you’re a Swiftie, I’ve got something special at the end for you as well.
Table of Contents
Discovering “Never Enough”
I first found out about Andrew on episode 63 of the Acquirer’s Podcast back in the heat of the COVID lockdowns.
As a long-time value investor and student of Warren Buffett, the analogy I’d use is that Andrew is the “Oracle of Victoria” in Canada, and Tiny.com is the Berkshire Hathaway of small internet businesses, spanning everything from coffee makers like AeroPress to movie review sites like Letterboxd.
As rotten as Rotten Tomatoes is, though, I’m too deeply invested in my profile there 🍅
Somewhere between 2020 and now, I started reading Andrew’s blog, listening to his podcast, catching his appearances on shows like My First Million, and eventually reading his book, Never Enough: From Barista to Billionaire.
If you ever listen to any of his public appearances or read his writing, he has an open invitation to grab a coffee. All you need to do is fly out to Victoria.
Luckily, I just needed to take a ferry instead of a plane 🛳
Make plans without expectations
Since Andrew’s blog first came out, I replied to over half a dozen of his emails.
Even though my messages were sometimes witty, fun, or insightful, busy people don’t have time to get distracted by everyone’s two cents, even when those cents are made of gold.
One day, I decided to be more deliberate and direct with my ask (paraphrased): “Can we meet if I get a ticket to Victoria?”
After a couple of follow-ups, a lot of patience, and a bit of luck, his assistant jumped in. I got invited to Victoria’s Entrepreneurship Lunch Club (ELC).
Though I was originally hoping for a one-on-one with Andrew, I figured there would be a ton of interesting people at the event and was equally excited.
I planned out the logistics, grabbed a Black Friday deal from clippervacations.com for a round-trip ferry and a two-night stay, and decided to make a mini-vacation out of it. Best part: I had no plans other than that lunch.
What followed was a quick arrival montage. I took the ferry Thursday morning and arrived at 11am. As I walked to my hotel, the vibe felt like a Canadian version of Manchester. Inside, I noticed a flyer for Butchart Gardens. Turns out it’s one of Victoria’s most iconic landmarks, and they were running a Christmas special. I explored the city, discovered Fan Tan Alley, the narrowest commercial street in North America at just three feet wide, and eventually made my way to Butchart Gardens. I caught up with some friends over the phone while walking the grounds. The colors were mesmerizing, and the seasonal exhibits were unexpectedly funny.
The next morning, heading down to the gym, I got a text from my friend Austin, the founder of Shinzo Labs. I had invited him to tag along for ELC, and he took me up on a last-minute offer to crash at my hotel. I worked out, he arrived, and we made our way to Part and Parcel.
When we arrived, Austin and I joked that we missed the memo that you need to be at least six feet tall to be part of ELC 🙃
We dove straight into conversations with the other entrepreneurs. One person had just moved from Vancouver to expand an in-person fitness brand focused on mobility, longevity, and explicitly not posting on Instagram. As someone who used to land in the ER every year until age 18, followed by a few career-ending injuries in my 20s, that immediately resonated.
Then the event kicked off, and the first thing I heard was: “Andrew won’t be able to make it today.”
My heart sank. I’d come all this way to meet him. Still, it was obvious within minutes that the room was exceptional, so I decided to make the most of it.
People introduced themselves, shared wins, and talked candidly about what they were building. One person casually mentioned that their SpaceX investment at a $30B valuation was looking pretty good given the rumors of a $1.5T IPO. I’m paraphrasing, but the caliber of the room was clear.
We broke into smaller groups with two simple rules:
One conversation per table
A set of prompts to guide the conversation
I found myself surrounded by seasoned founders who had built enduring companies across healthcare, mental health, adtech, identity, and more. The conversations were practical and grounded.
As things wrapped up, I asked Rajeev, who I’d been sitting next to, if he knew the best way to reach Andrew. He added me to the ELC WhatsApp group. After a short game of message roulette, message a few people hoping they were Andrew, I was eventually pointed in the right direction. I sent him a note and settled back into the patience game.
That evening, Austin mentioned some people from ELC may be attending a local comedy show. I remembered Andrew mentioning the same comedian in his last newsletter, so I grabbed a ticket, and we made our way to Jump Comedy.
We didn’t run into Andrew, but the day was still a success.
The next morning, while jumping rope at the gym, I got a response on WhatsApp! We set up a time to meet at a local nearby coffee shop at 1pm. My ferry was scheduled to leave at 5pm.
Should I buy a company?
We met at Hey Happy and got straight into it.
Since I already knew most of Andrew’s public story, the conversation naturally shifted toward filling in the gaps about me.
We talked about Vyvanse being an open secret among people with ADHD, along with the rest of our supplement stacks. At one point, he pulled about a dozen pills out of his pocket and lined them up on the table. As someone who’s been consuming protein powder, creatine, and BCAAs since 2005, I had a very clear reaction: this is my guy.
If you’re an entrepreneur, you’re probably a workaholic. That often comes bundled with an addictive personality, which spills into other areas of life, both good and bad. I’ve written more about that dynamic here.
By the end of the conversation, Andrew could tell two things. First, that I want to build deeply technical, meaningful companies. Second, that I don’t yet have the financial freedom to do that as effectively as I want.
That’s when he planted the seed.
Why not buy an existing company, clean up the operations, cut the burn, and extract whatever cash flow remains?
At first, the idea felt counterintuitive. How could a revenue-generating company need that much help?
Then it clicked.
There are plenty of founders who had a great run in a specific niche at a specific moment and would happily move on if the price, and a few other conditions, are right. There are also entire generations of small business owners who built something durable over decades and don’t know what the next chapter looks like.
For software companies, this playbook has never been more straightforward:
Review expenses and cut what you don’t need
Move bloated cloud workloads to bare metal
Automate obvious workflows with AI
Reduce the team to the true minimum
Start with something that already generates revenue and delivers value, and the rest becomes an execution problem.
I’m not looking to become a PE guy. I’m looking to buy time.
Time, freedom, and enough capital to take real swings at the big problems in this world, not just build good businesses. My mission in life is to help people reach their full potential, starting with myself. Buying leverage is just a means to that end.
That time doesn’t have to come from software. A traditional construction or contracting firm might be an even better candidate: steady demand, operational inefficiencies, thin margins hiding real opportunity, and almost no one applying modern tooling or systems thinking to it.
Optimize something boring. Buy freedom. Use that leverage to build the things that actually matter.
Showing Up, Building Relationships, Enjoying Every Moment and Making Things Happen
This trip worked out as well as it possibly could have, even though I had no real plan and accepted that my original goal might not happen.
I had a rough plan, one simple goal, and no expectations.
I wasn’t planning to explore Victoria, visit Butchart Gardens, go to a comedy show, or have anyone join me on this mini-adventure. I was planning to meet Andrew.
Up until the morning I was supposed to leave, expectations didn’t match reality, but I enjoyed every moment nonetheless.
I kept asking, texting, and nudging things forward. Instead of a group lunch, I ended up with an hour-long one-on-one. I met a ton of interesting people along the way and couldn’t have asked for more.
Reflecting on something I should’ve said better
One of the prompts at ELC was: “What is something you want to do less of?”
My answer: “Spend less time talking to investors.”
A bold choice, given the room.
What I should have said more clearly is this.
There are a few fundamentally different ways people approach capital:
Always be raising. Money is momentum.
Build something durable first, then raise to accelerate.
Optimize for independence and optionality, not scale at all costs.
My friction hasn’t been with investors as a group. It’s been with incentives.
Years in crypto exposed me to too many conversations centered on quick flips and zero-sum games. I’ve had people want to invest without understanding the product, and others ask me to build things purely for short-term speculation.
That’s not what I’m interested in.
I move fast. I care deeply about execution and revenue. But I believe investor returns should come after real value creation, not before.
If that closes some doors, they weren’t doors I wanted open.
Victoria Travel Recommendations
A quick list for anyone looking to replicate the trip:
Comedy: Jump Comedy, Ok Dope
Nature: Butchart Gardens
Tourism: Fan Tan Alley
Nerdy: Epic Games & More
Food: Al Barak Mediterranean
If you’re traveling from Seattle, I recommend a package from FRS Clipper that includes ferry transport and a hotel. I stayed at the Best Western Plus Carlton Plaza Hotel. Great location, service, room, and gym.
If you’re an entrepreneur, reach out to Andrew and his team at Never Enough.
Très bien
Cool story. Took a lot of guts and resourcefulness, way to go! The friction with incentives is something that many of us feel -- and all the better for those close doors! BTW there's a broken link: http://localhost:1313/posts/thoughts/2025-12-23-addiction-adhd-discipline-and-obsession.md