When I want to write but can’t — that’s how I know I’m going too fast.
It feels like I am here but have not arrived yet.
In my mind, a draft. A humpback whale of a tale surfacing into consciousness every other week.
I finally have time now; I bought it. Two weeks in Portugal, fully signed out of work accounts. All apps deleted.
Before I left, a friend asked:
When was your last real vacation? Selling your startup must be worth a one-month break or something.
So when was my last real vacation…?
July 2019. A week-long solo road trip to the Canadian east coast. Covid and work permeated all subsequent “vacations.”
Since that trip, I moved in with my girlfriend, became CEO, turned thirty, lived through a pandemic, broke the 1M ARR, sold Snipcart, managed the transition, bought and sold an unnecessary luxury car, became financially independent, traveled twice to Israel of all places, once to Colorado, and accepted a promotion as VP Product Marketing at Duda.
This all came with an unhealthy dose of anxiety, blues, conflict, and impostor syndrome. But also a healthy dose of confidence, gratitude, learning, and motivation.
Just listing these steps shortens my breath. I usually don’t handle change graciously. I need time to process, to feel in control of my story (however illusory that sentiment is).
Yet, these last years, I just… went with it. Macro pressures and incentives were too powerful. You can’t dodge a pandemic and shouldn’t pass on a life-changing opportunity. Sometimes momentum is the signal, and movement is the answer. Other times call for stillness and silence.
I find glimpses of the latter here, on vacation. It feels… unsettling?
Like I’m not doing what I’m supposed to — not taking care of business. Even though I know this is precisely what I’m supposed to do: nothing.
Idleness is scary. It frees room for demons to roam. Maybe that’s why I kept going so fast these last few years. Gave me excuses to not sit still and do the work.
Faster, faster, until the thrill of speed overcomes the fear of death. — Hunter S. Thompson
If you let it, modern life will throw at you enough stories to lose yourself.
Stories of reputation, nation, love, money, family, entertainment, career, religion, body…
It is painfully challenging to write your own. Some believe you can’t. Well, whether we land on free will or destiny, I think we should at least try.
A few weeks ago, I hastily tried to outline my next chapter. Now is a good time to finalize the contours of different paths forward.
There’s one thing I want to discuss first.
I’m aware money will now influence and even create life options for me.
Which is funny because I never imagined myself wealthy.
Younger, I had internalized laziness and high time preference. I often repeated, “I’m not that good with money,” reinforcing my struggle with saving. Or I’d just blame my impulsive nature. Some part of me also didn’t believe I’d make it past thirty. So why bother?
I did a lot of magical thinking around my Bitcoin holdings. I was lucky to have a friend who preached the Bitcoin news early. My meager investments amounted to a decent chunk a few years after university. I told myself I could always withdraw from this or use it later to buy a house. Bitcoin delivered on some of that magical thinking, but not all.
It was petty factors that forced me to start saving “regular” money more seriously. Indirect peer pressure. How did this twenty-three-year-old colleague own a house and two cars? I was twenty-eight, living in a cheap apartment with a car my Mom gave me. How did they afford to pay for a kid while I struggled to pay for a two weeks trip? I opened a Wealthsimple account, sold a bit of Bitcoin, and deposited funds here and there.
Then something less petty — being in a serious relationship. I realized my girlfriend, five years younger than me, had substantial savings already. We started discussing projects like buying a house, and the idea of not equally contributing felt uncomfortable. I started putting more money into a dedicated account.
Then something less petty still — living through a pandemic. I witnessed the inhumanity some of our elders went through. No fucking way was I going to let my mother alone in these care centers when she gets older. I called my financial advisor in the early days of Covid and set up automated transfers to long-term saving accounts.
It’s interesting how forms of fear motivated each step. I’ll keep the extrapolations for therapy.
More recently, a timely culmination of luck and effort — selling Snipcart in a bull market — increased my wealth drastically.
Money then became something different.
I had to find (pay) people to help manage it. I have a holding company now, diversified investments, credit lines, etc. I could have handled it by myself. Maybe. But it would have taken time and energy that I would rather spend elsewhere. I don’t like managing money. Even with professional help, I still need to dedicate a few hours per month to emails, light bookkeeping, calls, and meetings. I’m discussing fiscal strategy, portfolio diversification, cash flow optimization, life insurance, and succession planning.
This shit sucks. Of course, I’m extra thankful for the wealth I now have. Still, that admin part comes with stress that I was perfectly fine without.
One thing I like about having more money is the ability to be much more generous with people I love. Treating them to dinner, paying for some trips, offering cool gifts, etc.
Yet again, even this comes with a cost. See, new stressors appear:
- If I buy this more expensive gift, will it make the person uncomfortable?
- Will it irritate other people giving “smaller” gifts?
- If I invite my friend to dinner in a nice restaurant, will it look like I’m boasting
- Will they feel bad letting me take the bill?
- Will their pride kick in, making them insist on paying for themselves even if I offered first?
Again, I never imagined myself wealthy. So I have never even thought about these things. Yet they are now part of my life. It’s fucking weird.
What’s more, I used to despise wealthy people. My single mother barely scraped by and managed to put my sister and me through private school. So I grew up surrounded by many rich kids—nice parent cars, family trips overseas, latest skiing gear, etc.
I started washing dishes at thirteen years old, to dress as fly as them. For the first seven years of my “work-life,” I think I spent all my money on clothes, drinks, and drugs. All the while, hip-hop rags to riches narratives made me fantasize about, well… about many things.
I built up resentment. I didn’t have two parents, and I didn’t have a lot of money. Why did they? I started painting well-off people with the broadest of strokes. By the time I got to college and university, I would pick on my friends who came from wealthy families. Would tell them they had it easy. Would snicker at any sign of wealth: designer clothes, luxurious bags, fancy cars, big houses, flashy hotels, etc.
When I saw someone rich, I would assume they had 1) fucked people over, 2) inherited, or 3) shitty morals. Pricks, basically.
I was an asshole. I was young and hurt, sure. But I was an asshole nonetheless.
And now I’m rich.
(I laughed out loud writing this line alone in a Portuguese café)
I have not fucked people over nor inherited and have decent morals.
When driving around in my flashy new Benz, which I’ve now sold, I couldn’t help but wonder: is there a kid out there assuming I’m a prick?
I mean, for fuck’s sake, I’m shopping for houses in the same neighborhoods my friends’ rich parents lived in.
The traces of teenager left in my psyche tell me I’m a goddamn hypocrite.
The marks of maturity tell me something different.
That I’m in need of some kind of an identity update. Which type of “rich” adult do I want to be?
I need to grieve for that hurt boy’s old reality. To let it go, somehow. Then care for that boy still — I’ve healed some, but the pain remains.
I’m a man now, however weird typing this feels. I have responsibilities, people counting on me. People I can help, both with experience and money. The window for self-sabotage is getting thinner by the quarter. And that’s okay! I need to remind myself constantly. This new reality shouldn’t make me feel trapped; it should make me feel proud. Motivated. I’ve wanted to get my shit together for decades. Now, most of it is.
And the number one thing I can do to fulfill my responsibilities and help my people is to take care of myself. Hence, choosing a path that makes me happy is critical.
So I made a Google Sheet 😂
Through reflections and chats with friends, I accepted a temporary truth.
(That’s my new designation for things I might change my mind about.)
👉 It’s okay to separate personal passions from market opportunities. It’s cool to couple them if it makes sense, but it shouldn’t be forced.
Here are the potential paths I have identified:
1. Growing with Duda
→ Grow with the company. Take on new career goals in product or marketing. Delegate Snipcart management more.
I’ll develop on this one in conclusion ⏳
2. Pairing consulting with mentoring
→ Get involved more with Apollo13. Mentor startups, take on consulting gigs. Try to get early equity?
This path could offer more flexibility if a kid appears in the picture. I can see myself growing there, but not a lot. Hence, this would probably be a temporary option.
3. Launching a new startup
→ Pick a problem space I love. Bootstrap or fund? Hands-on with ops first 6-12 months.
This is really exciting. Risky, sure, but nothing existential. I’ve been drafting startup ideas in the mental health space. I’m confident I could gather talent and capital for a new venture. BUT, this is energy-intensive and a big commitment. Don’t know if I’m ready yet.
4. Getting a new job in tech
→ Get a senior position in product or marketing. Increase management experience and salary.
This would allow me to experience a new problem space while adding value quickly to the company. Probably get a compensation boost as well. However, it comes with a new culture, bosses, and colleagues. All things you can adapt to, but again, not sure if I’m ready for that.
5. Taking a creative sabbatical
→ Take a long sabbatical. Establish a creative goal to achieve — album, book, documentary? Set hard deadline. See if previous paths still relevant after.
Super exciting. Couldn’t do it without the money. Mom won’t like it, though 😂
Also, don’t know if I trust my lazy ass enough to discipline myself without clear accountability.
6. Investing full-time
→ Partner with others or existing funds.
I listed this one because the founder exits and starts investing narrative is omnipresent in startup land. I’m not excited by this. I said it earlier: I don’t like managing money. I also don’t have enough to sustain multiple hits and bear markets.
7. Switching careers
→ Take short sabbatical. Go back to school. Start new career course.
This is an interesting one. People reacted strongly and differently to it. Some friends told me it was the only worthy path. Said almost nobody could afford to do it, so I had the responsibility to try it out. Another said tech moves too fast, and I should get out before I became irrelevant. I disagree, but I respect their advice. Some people told me it was a bad idea, that I would waste all my experience, network, and skills by doing a full 180. Many problems and challenges in tech still excite me. I feel happy to be working in this space. If I stop feeling that way, switching careers might become more attractive.
As you know, I’ve chosen path #1 for now — growing with Duda. It came organically as the M&A progressed. I also have earn-out years to go through, so I thought making the most out of them by stepping up my career made sense.
I was very excited when I accepted the VP position. The amount of learning involved motivated me.
One month in, though, I’m struggling. I like the people, products, and problems I work with. I’ve learned more in four weeks than in the last two years. But I’ve also been smacked in the face with the workload, the number of challenges, and the current expectations inside the organization. I have two teams to build, product marketing and content. Five open positions. We have four product launches happening in the same quarter. Thank God marketing folks in Quebec are giving me a hand.
I’ve worked six days, 50-60 hours a week, some nights and weekends. That is not my jam. I guess it’s primarily self-imposed — I said yes to too many meetings and offered help on too many things. Wanting to prove myself early almost burned me out.
I’m hopeful things will stabilize. I’ll recover my life-work balance first. We’ll prioritize. We’ll build the teams. I have a new boss coming on board soon, CMO. Seems sharp and understanding, will see, might help. I hope it does.
I’m not the easiest dude to manage; I realize that. I’ll try to improve. I don’t like people telling me what to do, especially if it comes from a random notion of blunt authority. I care about people but couldn’t give less of a shit about their “positions.” My former boss and partner Georges had a particular management twist when I was younger, and making me more of an owner certainly helped.
Anyhow, it’s been liberating pouring all of these thoughts on the page. If you’ve read thus far, thank you. It was a big-ass update. Hope it inspired or entertained you.
I’m almost done.
I know who I am now, for the most part. So I’ll end with the question that matters most to me:
What feels meaningful in my life?
- Taking care of myself
- Helping people
- Telling stories
My path should enable all of these. I think the current one can. Still, I won’t wait three years again to re-assess!