Bombing my First Sequoia VC Meeting: A Humble Start to My Writing Journey

The backside of the business card we received from one of the Sequoia partners

"Do you have enough money for a follow-on investment in us?" That's the question I chose to ask the most powerful VC in Silicon Valley, Sequoia, right after they had exited WhatsApp to Facebook for a mere $16b.

Of course they had money!

While my initial impulse is to escape the memory's cringeworthy grip, there's a positive twist: it catalyzed my habit of capturing stories. The good. The bad. And the ones I’d most like to forget.

I primarily learn through listening to or reading others’ stories and admire those who master the skill of storytelling. It’s a powerful tool that bridges the gap between speakers/writers and listeners, making complex ideas relatable and memorable. Beyond being information delivery, stories hit you in the feels, share lessons, and leave a mark. I have always wanted to hone this craft but thought I had no stories to tell.

We all have stories to tell, even me. They were just hanging out in my head, unrecorded and quickly forgotten.

That would all change thanks to this defining meeting with Sequoia. Here's how it went down:

I was on my first trip to Silicon Valley, representing the mobile game studio Dirtybit as their VP of Business & Marketing with Nicolaj Broby Petersen, one of the co-founders.

Our breakout hit mobile game, Fun Run, was on fire, reaching 30m organic downloads and 10m monthly active users. We had managed to get an article in TechCrunch. We got plenty of momentum from it, both in terms of outreach and (surprisingly) app downloads. Most importantly, someone from Sequoia emailed Nicolaj to request a meeting with us while we were visiting Silicon Valley.

Our Silicon Valley advisor was ecstatic and exclaimed: "Founders would sell a kidney to get a shot at Sequoia." He was a local serial entrepreneur veteran with several fundraisers and exits.

What's the big deal with Sequoia? Sequoia is like the VC guardian of Silicon Valley. In addition to WhatsApp, they nurtured household names like Google, Apple, Airbnb, and Zoom to epic heights.

As the total newcomers we were, we dolled up as if we were Hollywood-bound for the Oscars. Nicolaj even bought a suit for the occasion, so we aligned with Norway's custom of dressing sharp for important meetings. Our eye-catching ensembles practically shouted 'outsiders,' standing out in stark contrast to the Silicon Valley founder crew's casual outfit of hoodies and shorts and the Patagonia vests worn by the VCs.

The California heat turned us into human waterfalls as we bussed up to their office on Sand Hill Road—because Uber was still a mystery to us, and we were too cheap to hail a cab. Despite being a profitable company, our student scrappiness was ringing strong in our ears as we had yet to understand the value of our time.

Despite our over-the-top attire, the meeting went well. Nothing fires the juices of VCs more than when they understand they are potentially first at scouting their next darling investment. Especially if the startup has yet to decide if they are raising or not yet. They made introductions to several of their portfolio companies to diligence them as a VC and asked at the end: 

"So, do you have any questions for us?"

Ahead of the meeting, we'd asked others for advice on questions to ask without revealing who we were speaking to. One of the pieces of advice we received was to ask where the investor was in their funds' lifecycle. If they were late, it could mean they couldn't allocate enough funds for a follow-on investment. A decent question to ask a VC if only:

1. I had truly understood what and why I was asking, and

2. I was meeting someone with one or few investment funds

As I pondered what to ask Sequoia, I felt the need to ask something. I remembered the golden nugget to ask about a VC fund stage, but I stumbled through it like a toddler learning to walk. They asked me to repeat the question as they hadn't understood it. That made two of us, so I rephrased it to something like, "Do you have enough money for a follow-on investment in us?" They exchanged a look that screamed 'confusion' and subsequent 'what's she been smoking?' but eventually confirmed they weren't broke.

As we left, our Silicon Valley advisor turned to me and said: "I wish you'd run your question by me before asking them in the meeting. Of course, they have money! It's Sequoia!" We would probably have raised something in the ballpark of $3-5m (although I don't remember what we discussed at the time). At that scale, a follow-on would be pocket change for someone like Sequoia. 

At that moment, I only heard: "That was a really REALLY stupid question to ask Sequoia."

While the Dirtybit founders ultimately decided not to pursue the fundraising path, when one door closes, another one opens. To ensure I'd remember and learn from my first real VC interaction and other experiences, Nicolaj and I entered a 30-day writing challenge, each writing at least one page in a mini notebook daily. Thanks to the writing habit that we developed over those 30 days, I can remember so much from my entrepreneurial journey and share the Megacool story with you (pun intended).

One of my journals from the past 10 years. Today these entries are digital.

Reflecting on our Sequoia meeting was the catalyst for my writing journey. We eventually laughed it off, envisioning the day I'd share the tale of my awkward Sequoia money question – and well, here we are. Sharing it with you, not just for shits and giggles but also to emphasize that mistakes don't define us, and we all start somewhere.

I'm no fundraising expert a decade later, and the learning never stops. But my habit of capturing these stories helps me see how far I’ve come. First fundraising attempts can trip up many entrepreneurs. Just remember, with time and plenty of practice, things improve. While I flunked my first fundraising meeting, I've later been part of closing over $65m in funding.

Now, tell me: what's your story?

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Many thanks to

Becky Isjwara

,

Latham Turner

,

Steven Foster

,

CansaFis Foote

and

Chris Coffman

for taking the time to read and gift feedback this week ❤️