5 years of founder grind

Disclaimer: People gave me “AI slop” comments on my latest article. I’m writing this post without AI, together with my co-founder Raffi and our content lead Finn who helped me edit it (“by hand”).

A lot of founders ask me whether they should apply to YC, open-source their product or move to SF. I get it, but I think we’re missing the real depth here. 

There’s pressure to work 996 (9am-9pm, 6 days a week), to be on top of the latest AI thing, to live in the right place, to “get it right”, according to strangers on Twitter. 

After 5 years of building Lago, I know founder life isn’t what it looks like on LinkedIn.

Exhaustion, isolation, frustration aren’t uncommon for founders and don’t go viral on X. 

But it requires more vulnerability than bragging about 10x'ing ARR.

The KPI of this post is: if even one founder feels less alone, it’ll be worth having written this. 

So here we go, a review of 5 years of emotions at Lago. How I got here, where I am and where I’m going.

From the outside, my story with Lago looks like a “normal” founder story: I left McKinsey to join a few startups early, built a product with my co-founder, got into YC and raised $22m. Then I moved to SF and now we have customers like PayPal, CoreWeave and Mistral.

And it’s true: We’re not a unicorn (yet), but I’m extremely proud of what we’ve accomplished, especially after spending our first 2 years in pivot hell.

But these 5 years weren’t a straight line, and neither were the years before it. Today, I want to give you a genuine, emotional look at these 5 years and everything that went into it.

I did not belong

It took me a long time to start a company, mainly because I didn’t view myself as the type of person who becomes a tech founder. Growing up in an immigrant family on a tiny island, I never would’ve dreamt of dropping out of Stanford (not that I went there).

I honestly didn’t know where I belonged. My family fled Vietnam during the war. They went where they could get a visa and scholarship, which happened to be San Jose, California.

Their lack of English proficiency and professional skills that didn’t translate well in the U.S. meant they never worked again. My grandmother never got a U.S. driving licence because her English was not good enough. I think they liked San Jose because they could stay within the Vietnamese community, where English wasn’t required, and their children supported them financially. 

When I say San Jose, I’m not talking about Adobe, Cisco and PayPal’s office towers. I’m talking about Vietnamese malls with Pho restaurants, grocery stores, and nail salons, where old people play cards in the parking lots.

My mother received a scholarship to study near Toulouse, in France, where she met my father. He loved wind- and kitesurfing, which eventually led my parents to Reunion Island (a tiny French island in the Indian Ocean) where I was born and grew up. Far away from any entrepreneurial ecosystem.

When your heritage is so complex, it’s hard to feel like you belong to any place or context.

My struggle with belonging extended into my professional life. My parents’ dream for me was a “safe” job in a big company. When we drove past PayPal and eBay offices in San Jose, I remember them saying these were good companies to work for. I guess this was their version of the “American dream”. 

So I tried to please them. Studied hard. I got into good schools. Got offers in banking, large corporations and management consulting. No matter how successful Lago gets, I still think my mother has never been prouder than when I tried to make sense of spreadsheets, footnotes, slides etc. at McKinsey.

I liked the learning, paycheck, prestige, and exposure to “strategic projects”, but didn’t feel like I belonged in this corporate world.

My parents were proud and everything was great objectively, I felt a deep mismatch. Everyday I was wondering is this really “it”? 

I never felt “ready”

I knew I needed to forge my own path, but had no idea where to start. So I quit McKinsey (yes, my parents worried), to learn from founders. Neither a series A startup, nor a later stage company made me feel ready.Even after helping a pre-seed startup blossom into one of Europe’s biggest fintech successes, I still felt like I needed something else..

I was about to take a job in a VC or apply to an MBA when one of my former bosses (a serial entrepreneur) told me: “You’re never going to be ready, what’s next, you’ll join a pre-IPO company, or a VC to learn stuff? It’s an infinite loop. Don’t miss out on your life.” 

This woke me up. I knew I had to do it now. I didn’t know how, but I’d figure that out. 

I didn’t have a mission or vocation

Some founders are fueled by a mission like "to organize the world's information and make it universally accessible and useful." (Google). Others have such deep expertise, their company is merely the culmination of their lifelong dedication to a craft.

I envied those founders, because I had neither.

I found something else that fueled me. The desire to build a home, a place where I’d love working. I didn’t feel like I fully belonged in any context I’d experienced, so I wanted to build a place where I did.

To me, the biggest perk of a founder is to choose who you work with: you co-founder, your team, the extended support system (fellow founders, investors, etc.). I’m not rushing to a potential financial outcome (being a founder is not the best way to build wealth…) or prestige (it’s not cool to grind that much, be irritable from stress and sacrifice parts of your personal life, believe me). But belonging made it worth it.The desire for a “home” was enough to start.

I knew the foundation for this home would be finding “Product-Market Fit”, and a large-enough market to support the people I wanted to accommodate.

Every founder needs something that fuels them through the 2am calls, constant rejections and self-doubt. 

For me, it’s building a “home”. For you it might be something else. 

Besides not belonging, there was another theme that kept surfacing.

I was paralyzed by comparing myself to others

You’re always going to be “the rich or the poor of someone”. There are founders and companies I’ve envied, wishing I could be like them. And I’m sure there are founders who wish they could be where Lago is. But there’s always going to be someone more successful, beautiful, wealthy and smart (at least from the outside). 

After 5 years, I know these “overnight successes” aren’t always what they seem. Countless companies vanished after flashy raises or celebrated launches. And many of the big successes took much longer than most people think.

For a long time, I was paralyzed by wanting to be “superhuman” like the founders that announced how they grew their company from 0 to $400M of ARR in 6 months.

Looking “superhuman” isn’t a guarantee of success. Massive, instant external validation, doesn’t make a successful company. It wasn’t healthy to compare myself to them, because I didn’t know what was going on behind the scenes. You can only see what’s visible, but not everything is.

The inverse can also be true. At my previous company, we struggled to raise a €1.2M pre-seed because nobody believed in the market. Now Qonto is mentioned as an example of a $5B+ unicorn, of which there are not many in France. Datadog and Revolut were rejected by YC. 

Many “overnight successes” took years of uncelebrated effort before they looked obvious. These years are actually crucial years where the “real moats” are built. 

External validation is one signal at a given time, but it shouldn’t decide whether your startup lives or dies. As an open-source billing system, Lago is building core infrastructure for enterprises. We now have tangible organic validation from this target, but during the first three years (it’s what it took to build the initial product), this was not the case. 

The product wasn’t big enough to cover enterprise use cases, and was too developer-focused and complex for SMBs and who valued “no-code” and “all-in-one” (and we thought this segment was already well addressed by the incumbents). 

So I’ve stopped letting that comparison become a judgment of myself. And decided to follow the conviction we had in our market positioning, while remembering what got me started here. 

I also get energy from a few other sources.

What keeps me going 

Being a founder isn’t easy. Your company dominates your life, your job is constantly changing. Everything’s urgent, you need to make team members, customers and investors happy… the list goes on. 

If I saw all of that in a job description, I’d never apply. But I’ve chosen to be a founder, and I love it. But I’ve seen in myself that you need to know what gives you energy, and make sure you get this in your startup. 

Here are my answers.

Choosing the right co-founder

Co-founder struggles are a massive reason for startup failure. If you lose trust when things get hard (they will), that can ruin a startup. Building Lago with Raffi was the most important decision I’ve made. 

There are a lot of obvious things we got right: We have complimentary backgrounds (business/growth and product/engineering) and already trusted each other’s work from our shared time at Qonto. 

But the most important thing we got right was the relationship. I think we do a good job of blending a co-worker relationship with a friendship, without drifting too far into one direction. 

We ensure we get non-work time together (playing sports, having dinner, etc.). While I met Raffi as a coworker, I highly recommend Gloria Lin’s cofounder dating playbook if you’re looking for “the one”.

Focusing on the inner fire 

I love building with Raffi and our team. I like the craft, the ruthless culture of self-improvement, the relentless energy we put into solving problems, and the pride we take when we overcome adversity.

The reason we made it through the pivot without losing some of our earliest hires, was that I always knew we had whatwe needed to succeed,  but needed “product market fit” (PMF).

After 2 years of grinding to find  PMF (yes, it took 2 years!), Raffi and I thought: “That’s the hardest thing we’ve ever done, now we can build the company we want as a home.”

Trusting my team that we can make it through the worst (and pivoting was rough) is my inner fire, it makes me feel alive regardless of market swings. Even if Lago keeps changing, it gives me a lot of stability.

This feeling of belonging is my internal fire. You might find yours elsewhere, there’s no rule.

Cultivating high agency and luck 

Building a company is about expanding your surface area of luck. Being in charge of my own fortune. I don’t want to be a manager of the circumstances life gave me. I tried to write a paragraph about this, but realized nobody would articulate it better than Swyx in his essay.

Nurturing and valuing depth in connections

Building a company is a multi-year journey. It may take 2 years, 5 years, 10 years or even outlast you.

I don’t believe in sacrificing everything until you reach some imaginary finish line like an acquisition that makes you rich.  So many founders abandon the rest of their life because they believe they’ll be rich soon and can catch up on everything. This sometimes works. But you don’t hear of the many founders who burn out and watch their companies disintegrate.You need to accept that beating the odds (most startups fail) means mobilizing extraordinary resources. I want to  is to create a setup that’s sustainable (and enjoyable!) for 10+ years. 

I don’t have a magic formula for this, but here’s a few things that stuck with me (heard from mentors and friends): 

• “There are “deal friends” and there are “real friends "
• “You can’t be a good founder if you’re a miserable human”
• “Let’s say your business does incredibly well, who would you like to share the news and the fruits of your labor with?”

There’s a few people in my life I want to consistently show up for. They may or may not understand tech or entrepreneurship. But they make me feel grounded, connected, and “alive”.

I make a point of being fully present ( this means quality time, switching off the “war CEO founder mode”) with and for them, and not making them feel like “second class citizens”.

There’s always going to be unforeseen events or changes in a startup, I want these people I’ll be here no matter what. 

Overall, I value depth over width. 

These were some of the reflections of the emotional journey of being a founder over the last 5 years. I genuinely hope they were useful or at least can resonate with someone you know. (I need to hit my KPI! :) )