How I Work
By Willson Cross
To save us both time, I've written this essay so that anyone considering a role at Borderless AI can understand my work style and what it's like to work with me. It is important that potential team members grasp my approach before joining the company, rather than discovering six months in that it might not be a good fit.
The first thing anyone should know about me: I do my best to not go to bed at night with any customers left in the lurch. That’s the baseline. Everything else flows from that.
Am I slow responding to a vendor, teammate, or investor sometimes? Sure. That’s not ideal, but I can sleep fine knowing that. What I can’t sleep on is knowing there’s a customer out there who’s not pleased and hasn’t heard from us. A simple “We understand your concern and will get back to you first thing in the morning” is better than any sleeping pill. That message takes 30 seconds. If you work with me, you’ll learn fast that customers come first — not in a poster-on-the-wall way, but in a “this is why Willson is texting at 11 PM” way.
If you're not responding to important customer inquiries in an appropriate time frame, or at least informing management that there's a customer needing an answer, I view this as a slow company killer.
I’m a text and phone call guy
If I need something from you, you’ll get a text, a voice note, or a quick call — not a calendar invite for next Tuesday. I’m a big fan of voice notes. They’re faster than typing, more personal than text, and the other person can listen on their own time. I will certainly not wait for a meeting or our upcoming 1-on-1 to speak with you about an urgent item. And it turns out, I’m in good company.
Brian Chesky at Airbnb ditched email, banned meetings before 10 AM, and replaced most formal one-on-ones with quick phone calls and texts. His take: “[Emailing] was the thing about my job that I hated the most.” Instead, he calls. He texts. He keeps it moving. That’s my language.
Bob Jordan, CEO of Southwest Airlines, blocks every Wednesday, Thursday, and Friday afternoon on his calendar — no meetings allowed. He said it plainly at the NYT DealBook Summit: “When you first start, it’s easy to confuse busyness and going to meetings with leadership” and “there’s no time to ‘work,’ and you confuse going to meetings with the work.” Those blocked hours are for thinking, calling people, and doing the actual job.
Elon Musk sent an email to all of Tesla telling employees to walk out of meetings that don’t need them: “Walk out of a meeting or drop off a call as soon as it is obvious you aren’t adding value. It is not rude to leave; it is rude to make someone stay and waste their time.” He called excessive meetings “the blight of big companies.”
Jeff Bezos is famous for his structured meeting rules at Amazon — no PowerPoint (replaced with six-page memos read in silence), the two-pizza rule for team size, and junior people speaking first. He once called banning PowerPoint “probably the smartest thing we ever did.” But what I admire most is that he’s skeptical of polished meetings: “I am very skeptical if the meeting’s not messy.” Real work is messy.
Jensen Huang runs Nvidia — a trillion-dollar company — with 60 direct reports and zero routine one-on-ones. His reasoning? “I don’t have one-on-ones with them because it’s impossible. We present a problem, and all of us attack it.” He doesn’t want anyone getting secret intel or special access. Everyone operates with the same information, out in the open.
Steve Jobs kept meetings small and ruthlessly on-point. Ken Segall, who worked closely with Jobs at Apple, recounts a story where Jobs spotted someone unfamiliar in a weekly meeting, asked who she was, and politely told her: “I don’t think we need you in this meeting.” No spectators. If you’re in the room, you’re essential. If not, you’re out.
My take on the above quotes
I'm not trying to be like any of those people. My goal isn't to be them. I’m just giving you some food for thought.
Please know I don't read the quotes above and go, "Oh yeah, that's me. I'm gonna be just like them." … That's not my style. I just think those quotes are a good illustration and guide for folks to get a sense of how I may operate from time to time.
Personally, what gets me up in the morning is having a much more than zero chance of building a profitable, $100 million ARR business. My personal goal, maybe a bit of an ego thing, is to be seen as a really sharp business person running a super tight ship. So, nailing this well-run business thing is a big deal for me.
I've got this thing I call "elevator calls." Seriously, a productive phone call can be over in the time it takes to ride an elevator. I'm literally on calls in elevators, taxis, on the train, and while walking to the airport. Most important conversations don't need a full 30 minutes; they need two.
The moment I arrive at my desk, my routine is to dive immediately into my emails, Slack messages, and texts, embracing whatever challenging news awaits me in my inboxes.
From the moment I wake up until I arrive at the office, my phone and computer remain off-limits. I keep my phone on airplane mode and out of the bedroom until I've reached the office, which is when I finally check it – I get into the office at 6:30am / 7:00am most days.
I find anywhere I need to travel to for business, there's usually a WeWork in that city, so I make sure my hotel is as close as possible. I follow the same routine no matter what I got going on that day. I always start at the desk at 6:30am / 7:00am.
Bad news first. Always.
“If you are going to eat shit, don’t nibble.” - Ben Horowitz
I want to hear the bad news first. In fact, I don’t care much about hearing good news at all – It's nice to hear, but it doesn't do much for anyone when we're at a stage of ferociously building. What I care about is what’s broken, what’s stuck, and what needs fixing.
At the scale we’re at, there is bad news every single day. There are things to improve on every single day. I expect to hear about it. That’s not a failure — that’s the reality of building something (I'd say failure is if the same bad news is happening daily, weekly, etc..). If there’s a customer that’s gone unanswered, an issue that’s been building up, a fire you don’t have the solution to yet, something you’re blocked on, or something you simply don’t have the bandwidth to get to — I need to know.
You don't need to have the perfect solution before you come to me. Please, just don't sit on things. Silence is what truly hurts. The problem itself is rarely the biggest issue—the real concern is when I find out about it days later because someone was hoping it would magically disappear. It won't. Bring it to me early, no matter how messy it feels, and we will absolutely sort it out together. That open, early communication is how we build a strong sense of trust.
You will never spam me or “bug” me – just call! I’m at 604-889-7532
I run 996. You don’t have to.
There’s a concept from Chinese tech culture called “996” — 9 AM to 9 PM, 6 days a week. Jack Ma called it “a huge blessing.” It sparked a massive debate. (Source: CNN)
I know 996 has been making the rounds on Twitter and LinkedIn lately like it’s some new discovery. It’s not new to me. I’ve been talking about this since my mid-20s. I pretty much run 996 on myself. Not because someone told me to — because I want to. Building a company is the thing I think about when I wake up and the last thing on my mind before I sleep. Weekends blur into weekdays for me, and I’m fine with that. Will this be me forever? Maybe not. But right now, in this chapter — this is exactly where I want to be and exactly how I want to be doing it.
But here’s the important part: I do not expect that of anyone else.
Most team members generally work a standard 8:00 AM or 9:00 AM start time, leaving between 5:30 PM and 6:30 PM, but they often check/lock in online again before bed.
While weekend work is rare, I do occasionally have ad hoc weekend calls (about twice a month with a couple key execs), and if a critical issue arises, I expect the team to be available.
Expect 2-3 late evenings per month where we order dinner and work until around 9:00 PM.
I truly don't think this is too much to ask for – and if we were to be successful, it wouldn't really add up if we got successful without doing the above
My pace is my pace. If you do great work in your hours and you’re responsive when it matters, I have zero interest in whether you logged on Saturday morning. I’d rather have someone sharp, happy, and rested than someone grinding themselves down trying to match my schedule. I want people who are energized by the work, not burned out by it.
The worst version of 996 is when a founder runs at that pace and silently expects everyone to do the same. I’m very aware of that, and I actively work against it. You’ll never get a passive-aggressive text from me because you didn’t respond at 10 PM on a Sunday. That’s my time to be on. It doesn’t have to be yours. I care about the people I work with, and that means respecting how they recharge.
My actual working day:
- 6:30am / 7:00am: Get into the office
- 3pm, 4pm, 5pm: Sometime during this range, I might disappear for an hour for a run or gym, but this is honestly only a couple of days a week.
- 6pm: dinner in office
- 7pm: I leave office to hang with my wife before 9:30pm bed
On Saturday mornings, I go for a walk with my wife and dog – then go into the office where I have a 2-3 hour call with my co-founder and work until date night.
What this actually looks like day-to-day
The tools I live in: iMessage and phone calls for fast communication. Signal for my senior leadership team — it’s our dedicated channel, separate from everything else. Loom for walkthroughs. GSuite for docs. Claude for thinking through problems. Replit for spinning up quick prototypes and internal tools. Granola for capturing the meetings we do have. Zoom when we need face-to-face — I prefer it over Google Meet. That’s the whole stack.
What’s not on that list: Notion. If your workflow depends on building a wiki with 47 nested pages before any work gets done, we’ll have a friction point. I’m also lukewarm on Slack. For large-scale projects with multiple people, it works. But for day-to-day one-on-one communication? It’s meh. I’d rather just text you or call you.
I love Google Docs — especially the comment tool. It’s one of the fastest ways to give feedback without scheduling a meeting or writing a novel. Drop a comment, tag someone, done. That’s collaboration without the overhead.
On email: I read all of them. I don’t respond to all of them. And I’ve probably sent an email longer than a paragraph a handful of times in the past year. If something takes more than a paragraph to explain, I’d rather just call you.
Your phone will ring sometimes. It’ll be quick. If you can’t pick up, I’ll text you what I needed.
Loom is your friend. Record a walkthrough, I’ll watch it at 2x and respond with a text or call. Way faster than a 30-minute screen share.
You won’t always get full context up front. Sometimes I’m moving fast and I need you to run with what you have. The context will come. If you’re okay starting with 60% of the picture, you’ll do great here.
If you need to explain something to me, use an example. Don’t give me a paragraph of theory. Show me. “Here’s what happened with Client X, here’s what I think we should do, here’s why.” That lands in 10 seconds. A wall of abstract reasoning doesn’t.
Expect the unexpected call. I might call from an airport, a taxi, or between floors in an elevator. The work is serious. The process doesn’t have to be.
1-on-1s
I do 1-on-1s. I usually have Granola running during them. When we’re done, we take five minutes together to summarize the action items. Then I take the Granola notes and add them to our shared Google Sheet — nothing fancy, just a running list of what we talked about and what needs to happen next. No dedicated app, no project management tool. The conversation matters more than the format. I have the Google sheet hyperlinked in each calendar invite for us.
Your first 90 days
What might seem super small and simple to you, may be a big deal to me. If you're early in your time with us, there won't be much shared context yet.
I need to work very closely with you for the first few months. That’s non-negotiable — and honestly, it’s one of my favorite parts of bringing someone new on.
During that time, I’d like us to stay close on any action before we actually take it. Not because I’m second-guessing you — because alignment matters more than speed in the beginning. Here’s a real example: an executive on day seven emails a very big customer, thinking it’s the right thing to do. Maybe it is. But it would have been great if they’d checked in with me first. Not for permission — for context. I might know something about that relationship that changes the tone, the timing, or whether we reach out at all. We need to get on the same page about how we think, how we communicate, and how we make decisions together. Once that’s locked in, you’ll have all the room in the world to run.
You need to learn how I communicate — that a short text isn’t me being cold, that a random call isn’t me micromanaging, that silence usually means I trust what you’re doing. And I need to learn the same about you. By the end of those first few months, I should be able to send you two sentences and you know exactly what to do with it — and you should feel comfortable pushing back when I’m wrong. That’s alignment. Everything after that gets easier.
Ask anyone who’s worked with me long enough and they’ll tell you: autonomy is real. But it’s earned in those first few months, not handed out on day one.
I’m a big fan of frugality
I make it very hard to spend money at the company. Frugality is a discipline, not a constraint.
Imagine you put the company credit card in a brick of ice. By the time it melts, would you still make that purchase? If yes, go for it. If the urgency disappeared — it probably wasn’t a real need.
Charlie Ergen, the founder of Dish Network. Billionaire. Office furnished with secondhand couches. Doesn’t fly first class. Still personally signs every check over $100,000. Packs a brown bag lunch every day. I slant heavily toward that mindset. (Source: Inc.)
Frugality forces creativity. We don’t pay for tools we can build. We don’t hire for a role when the real fix is a better process. Every dollar we don’t waste goes toward the product, the customers, and the people doing the work. That’s not a budget policy. That’s a value.
The tradeoff (because there is one)
If you like a lot of structure, daily check-ins, and someone telling you exactly what to do next — you’ll probably feel lost here.
But if you do your best work with room to breathe, get energized by moving freaky fast, and would rather do the thing than talk about doing the thing — I think you’re going to love it here. And I’d love to work with you.
Want to know what it’s really like to work with me? Ask someone who has:
Sean Aggarwal, Alec Andronikov, Dave Bustos, Derrick Isaacson, Armaan Kanani, Gavin Mah, Umesh Maini, Omeed Malik, Peter Mueller, Paul Ratchford, John Salama, Dora Sauder, Nate Sauder
*listed in last name alphabetical order
Check out our podcast here – It might give you more of a vibe when working with me.
A note on in-office work
A lot of what we do at an early stage is eliminating how risky building a startup is. I like to think about our jobs as de-risking the proposition of building an early-stage funded technology company. And I think being in office de-risks this a lot.
Jeff Bezos once shared advice he got from investor John Doerr:
"What startup companies do is they take their precious early-capital dollars and systematically eliminate risks. That's what the successful ones do."
We are building a lot from scratch, so a lot of things we do is high risk. If we're in the office, it's going to de-risk things.
So much is outside our control, we should focus on what is in our control. And that's where Sam Altman's point comes in:
"I think definitely one of tech industry's worst mistakes in a long time was that everybody thought they could go full remote forever, and startups didn't need to be together. There was going to be no loss of creativity."
"The more unclear and early the product is, the more in-person time the team needs to grind together."
That's why being in office matters. As much as it's a policy, it’s a strategy. It's how we de-risk.
A note on Toronto
I’m building from Toronto. I think it’s a top-10 city to grow a company, but not top-3. The engineering and product talent here is exceptional — genuinely world-class. Where it gets harder is on the go-to-market and customer success side. Most of the GTM and CS folks in this market haven’t seen Valley-like scale. They’re smart, they’re hungry, they’re capable — but the reps at that level just aren’t as common here yet. Toronto’s also not the hardest-working city I’ve seen. A typical WeWork in New York or Munich is buzzing at 8 PM. That’s never the case in Toronto. That’s not a knock — it’s just the reality of building in a market that’s still maturing and housing folks that have seen massive scale.
A note on raising money
Terms. Terms. Terms.
If you’re going to raise, the terms matter more than the amount. I've raised money every 10 to 15 months for the last 10 years of my life, and when terms are good, it makes all the difference in the day to day ebbs and flows of doing startup life.
I know this is sort of obvious to say, but I think most terms are bad. And in my experience, it almost makes it not worth doing a startup if you have to do bad terms.
I care way more about being unknown and profitable than I care about being in TechCrunch or The Information with lofty investor headlines.
That said — if you truly believe you have a shot at being the category leader, then I could see how it would make sense to raise as much and as fast as you can; at “sort of whatever terms”. At that speed and scale, maybe the terms won’t matter as much because the outcome overwhelms everything else.
But if you’re going to take your time — if you’re going to cockroach your way to $25M, $50M, $100M ARR — be very careful about how much you raise and on what terms. Every dollar you take in that scenario is a dollar you’ll feel later. Dilution compounds. Bad terms compound faster. The frugality section above isn’t just about office snacks and SaaS subscriptions — it’s about building a company that doesn’t need to raise on someone else’s timeline.
