From 6 AM Meetings at Starbuck to Joining Amplitude, a Founder's Story with Enzo Avigo

What does it really take to found a company?

Courage, guts, and a lot of hope. You've got to jump into the unknown and move fast because time is your biggest enemy.

Today, we're learning from someone who lived this reality for five years. No shiny rainbow, just the reality of founders in the trenches.

Former Intercom Product Manager, Enzo Avigo, knew what he wanted. He dreamed of having his own company. He spent over five years building June.so, a B2B SaaS analytics platform that started with 6 AM meetings at Starbucks and ended with joining Amplitude's team.

What sets this conversation apart is Enzo's willingness to share the critical details most founders keep private. His story dismantles many of the polished narratives dominating startup advice today.

Enzo openly shared his experience navigating Y Combinator, raising funding, and ultimately making the difficult choice to sell, which provides rare insight into both the entrepreneurial journey and the acquisition process.

For anyone building a B2B product, struggling with market positioning, or curious about what really happens when startups join larger companies, this episode delivers practical wisdom earned through years of real-world experience.

Here are some nuggets of knowledge you’re going to get from this episode.

7 Key Takeaways from the Episode

1. Find Your Co-Founder Through Direct Outreach

"I remember watching a video from YC at the time that said that the best way to find a co-founder is to go through your network, maybe LinkedIn, and list five people you think you would be interested to work with and message them in the next 24 hours."

Enzo's practical approach to finding a co-founder involved identifying five people from his network and reaching out within 24 hours. Surprisingly, his co-founder turned out to be a colleague at Intercom whom he already worked with daily, proving that sometimes the best partnerships are hiding in plain sight.

2. Most Startups Don't Segment Deeply Enough

"We didn't niche down enough. We always assumed that a segment was a niche, while it wasn't for our product. Initially we're like, okay, let's focus on early stage startups. And then we're like, okay, let's focus on early stage startups that are product driven. And then we're like, startups, product driven, B2B SaaS. And then at the end we were like, B2B SaaS, Vertical SaaS."

Enzo's biggest mistake was thinking basic segmentation was enough. It took years to realize they needed to go from "early stage startups" to "product-driven B2B vertical SaaS companies" to achieve true product-market fit.

3. Your Most Active Users Aren't Always Your Best Customers

"The people that will pay for your product are not necessarily the ones that are the most active in your product. We found out that not all problems were equal."

When June introduced monetization, they discovered that usage intensity didn't correlate with willingness to pay. B2B customers with bigger problems were willing to spend significantly more than highly active users with smaller pain points.

4. Moving Upmarket Requires Intentional Strategy

"Unless you say like, no, this is the amount of work we're willing to put into owning the startup segments, and we're going to go intentionally to seed series A, series B, you're going to end up in some sort of depth loop where you stay in your existing market forever."

Enzo learned that without intentional planning to move upmarket, startups get trapped serving their initial customer base forever. The endless feature requests from existing customers can prevent the focus needed to graduate to higher-value segments.

5. Social Media Trends Stop Working When Everyone Adopts Them

"Now, if you look at videos done by startups, they're recorded by cameras that cost close to 10K. They were great three years ago because it was really uncanny, but now it's standard and everyone is doing it."

Enzo warns against following visible trends on platforms like LinkedIn. By the time high-production videos became standard for startup announcements, they lost their power to capture attention because everyone was doing the same thing.

6. Choose Your Distribution Channel Based on the Message It Sends

"The medium you're using already communicates something about your product. If you see a video of a startup that has raised money on LinkedIn, it's a whole different feeling than when I found out products like Linear on Twitter."

Different platforms convey different messages about your product before users even hear your pitch. Finding Linear on Twitter felt like discovering a secret tool for early adopters, while LinkedIn announcements feel corporate and mature.

7. Acquisition Can Be About Impact, Not Just Exit Strategy

"How many companies are going to be using June next year, in two years, in five years? How much can we change that inflection point? And how much impact would we have if we joined forces with someone who has realistically more impact than us?"

Rather than viewing acquisition as a failure or simple exit, Enzo framed joining Amplitude as a way to increase their impact. Sometimes the most ambitious path forward involves joining forces with a larger player rather than going it alone.

Share your thoughts in the comments.

Let’s keep untrapping the product world together.

Talk soon,

David Pereira

100XPM Mastermind

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