Cash Flow Positive: Lessons from Enzo Avigo on Prioritizing Profitability Over Fundraising

At our founder event series, we had the pleasure of hosting Enzo Avigo, the founder of June.so, for a deep and refreshingly honest conversation about a topic that's becoming more and more relevant in today's startup world: prioritizing profitability over fundraising or chasing fast exits.

This session, part of our ongoing series organized by the beams team, explored how Enzo led June to becoming cash flow positive — and why focusing on financial sustainability can sometimes be the smartest move for early-stage founders.

From Seed Funding to Cash Flow Positive: The Journey

Enzo kicked off by sharing june's early story:

Starting lean: With just two founders and no financial cushion, they raised a small angel round ($50k) to survive the first months.

Y Combinator breakthrough: After building early traction, June raised a modest $1.6M seed round after YC demo day—despite being offered much more during the 2021 funding boom.

Intentional constraints: Rather than overspending, they deliberately kept their monthly burn around $50k, giving themselves a 3-4 year runway to find product-market fit.

This discipline set the stage for June’s later success. As Enzo put it, "Operating under constraints forces you to figure things out."

Finding Product-Market Fit—Twice

The journey wasn’t straightforward. Initially, June positioned itself as a simple, plug-and-play product analytics tool for early-stage startups. But they eventually faced a choice:

Double down on small customers (high churn, small contracts), or

Move upmarket to serve Series A/B startups, offering deeper analytics and CRM integrations.

They chose the latter—and with it, revamped their pricing and packaging, tripling their average contract value (ACV). It wasn’t easy: June had to sunset their free plan, deepen customer conversations, and streamline onboarding.

Why Go Cash Flow Positive?

A key turning point came when June’s runway shrank to around 18 months. Rather than scrambling for a Series A in a tough fundraising climate, Enzo and his team made a bold decision:

Focus on becoming cash flow positive by controlling burn and optimizing revenue.

Trade a bit of speed for control, knowing it would buy them crucial extra time to iterate without external pressure.

Implement yearly upfront payments, dramatically improving cash flow with each new customer.

Enzo summarized the mindset shift perfectly:

"What you really want as a founder is enough cash to iterate as many times as necessary to figure it out."

How Investors (and Acquirers) Reacted

Going cash flow positive changed external conversations too:

Private equity funds and SaaS rollups showed strong acquisition interest.

Traditional VCs became less reactive, preferring to chase hyper-growth (especially in AI).

Strategic acquirers (those looking to integrate tech) were less aggressive, assuming June would now run independently longer.

For June’s own board and early investors, though, the move to profitability was a net positive. It demonstrated capital efficiency — a powerful signal in today’s cautious market.

💬 Final Thoughts: Key Takeaways for Founders

Enzo closed with an important piece of advice for fellow founders:

Always plan for the number of iterations you’ll need to reach strong product-market fit.

Budget enough runway for those iterations — whether through fundraising or careful cash management.

Don't jeopardize growth if you want to stay attractive to VCs later — but remember, sustainability can buy you the time you need to build something meaningful.

In short: Cash flow positive doesn’t mean giving up ambition — it means giving yourself options.

Thanks again to Enzo for sharing his story with raw honesty — and to all the founders who joined live! Stay tuned for more events helping you navigate the realities of building lasting companies.

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