Lessons from leading investors for angel ready to level up
Early-stage investing is exciting and unforgiving. Startups pivot, markets shift and data is always incomplete. For angel investors, the challenge is not access to deals, but learning how to make consistently good decisions in an environment where certainty never exists.
Over the past months, IAG set out to answer a simple but ambitious question:
How do the people who have been allocating capital professionally for years actually think?
Through Venture Play, we brought angel investors into direct conversation with partners and senior investors from worldwide tier-1 VCs: people who have built portfolios over time, navigated cycles, made mistakes and produced tangible results in early-stage investing.
The goal was not inspiration, nor theory. It was exposure. Learning directly from those who do this work every day, under real constraints and with real accountability. Different geographies, strategies and styles, but all facing the same structural realities of venture capital.
This article distills what emerged from those conversations. Not as a recap of the program but as a set of actionable insights for any angel investor looking to professionalize their approach and increase their long-term impact.
Invest in people, not plans
Early-stage ideas rarely survive contact with reality. Markets move fast, assumptions break and data is scarce. What matters most is how founders respond under pressure. Execution, judgment and integrity outweigh the initial idea.
Curiosity and continuous learning improve judgment over time. Observing, asking the right questions and immersing yourself in new sectors lets you anticipate emerging opportunities. Backing founders who can adapt strategically is far more valuable than betting on flawless pitch decks.
Dealflow and networks are your real advantage
The best angels see dealflow not just as a pipeline of opportunities, but as a learning engine. Reviewing many startups teaches you to spot quality when it matters.
But relationships are what truly multiplies your impact. Strong networks connect founders to people, knowledge and opportunities that money alone cannot provide. Investing time in building trust, sharing expertise and linking founders to the right resources is how you create outsized results.
Pro tip: Don’t just meet founders - connect them with mentors, partners and potential customers. That’s where real value is created.
Power Law thinking
Most startups fail, some return just enough and a tiny fraction deliver massive returns. Understanding this reality changes how you invest: it’s not about being right most of the time, it’s about structuring your portfolio to capture the rare winners.Timing, sizing and disciplined reflection turn chance into repeatable advantage. Keep a record of your decisions and learn continuously from every investment.
Embracing uncertainty and possibility
Angel investing thrives at the edge of the unknown. Following the market that’s already paved is easy. Taking creative risks is what separates those who build successful startups from those who fall behind.The most impactful angels spot opportunities where others see danger, act decisively and help founders turn challenges into growth. Facing uncertainty with insight transforms risk into tangible results and helps shape the future of the ecosystem.
Applying the VC Mindset
Thinking like a venture capitalist means reasoning in portfolios, making structured decisions under uncertainty and applying rigor to amplify intuition. Effective angels are hands-on, strategic and collaborative. They add value through networks, engagement and guidance (not just money). Structured support and mentorship accelerate founders’ growth, creating value that goes far beyond capital. The best investors combine judgment with courage, structure with intuition and capital with influence. They step into the unknown and help founders turn possibilities into reality.
Leading the way
What emerged most clearly from this journey is that professionalizing angel investing means internalizing venture capital discipline: slowing down decisions, thinking in portfolios, questioning assumptions and accepting that uncertainty is not a flaw of early-stage investing, but its natural state.
For those who took part in this experience, the real work begins now. Applying these principles deal after deal, reflecting not only on outcomes but on the quality of each decision, and being deliberate about where capital, time and energy are deployed.
This is where angel investing truly comes alive - at the very beginning, between uncertainty and possibility. Stronger ecosystems are built by angels who raise their own standards first, who see potential where others see risk and who actively help founders turn challenges into opportunities.
The question is: will you be among them?
If you think IAG’s role in this journey ends here, it may be time to rethink that assumption.
The journey continues… and it’s expanding!
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Thank you to the funds and the super angels that participated in Venture Play; your involvement made it truly impactful!
- Italian Founders Fund
- Heartfelt
- Founders Future
- Left Lane
- Runa Capital
- 10x Founders
- Luca Ascani
- Armando Biondi
- Speedinvest
- Rancilio Cube