Inside An Angel Investing Network: Strategy & Opportunity with Marty Isaac EP 130

Dec 1, 2025

Marty Isaac, President and Managing Director of the Angel Investor Forum, offers insights from his wealth of experience in angel investing. He stresses the importance of diversification, recommending at least 20 investments to better capture successful ventures. Marty also highlights that successful investing now requires proof over mere ideas, emphasizing the significance of the management team. Additionally, he discusses the supportive community within angel groups and sheds light on opportunities for women founders through initiatives like Haven Hatch.

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ANECDOTE

From One Big Bet To Many Small Bets

Marty accidentally invested too much in a friend's startup early on and doubled his money.
That experience taught him to diversify across many cap tables rather than join one company full-time.

INSIGHT

Power Law Drives Returns

Angel investing carries extreme downside: about 50% of startups go to zero and another 20% don't return capital.
Returns depend on the power law where a few outsized winners produce most gains.

ADVICE

Diversify Aggressively

Diversify: aim to make roughly 20 investments over five years or join a fund to spread risk.
This increases the odds of hitting an outlier winner that offsets many losses.

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In this episode of the HAYVN Hubcast host Nancy Sheed talks with Marty Isaac, President and Managing Director of the Angel Investor Forum, Connecticut's leading network of early-stage investors. Marty brings a refreshing, community-minded perspective to angel investing — one built on curiosity and collaboration.

"There are no sharp elbows in our group. We all want the companies — and each other — to win."

A former GE and consumer marketing executive turned investor and civic leader, Marty shares how he built his portfolio — from early, overzealous investments to smart, diversified "small bets" — and why he's so passionate about supporting founders and helping build strong management teams.

Key Points

Angel investing isn't just for the ultra-wealthy anymore — while investors still must be accredited, angel groups and diversified funds have made participation more accessible and structured.
Risk is extremely high, with 50% of early-stage companies failing and another 20% not returning capital — which is why the power law (a few big wins) drives overall returns.
Diversification is essential, with Marty recommending at least 20 investments over five years or participation in a fund to increase the odds of catching an outlier success.
What angels look for comes down to three fundamentals: the problem, the solution, and how the business makes money — but the management team remains the most critical factor in determining whether a company can execute.
Proof Over Ideas: Today's investors no longer fund pitch decks alone — lower startup costs mean founders are expected to show real traction through proof points like customer validation, pilot programs, or early revenue to demonstrate market fit before attracting capital.

Marty's insights offer a grounded, practical look into the realities of angel investing today — from the risks and rewards to the strategic thinking required on both sides of the table. He also shares what's happening in the broader world of angel investing — from how Connecticut's startup scene has grown to what investors are watching closely right now.

Whether you're a "founder" seeking capital or an "investor" exploring the startup ecosystem, Marty's candid reflections and open arms optimism make this conversation educational, energizing, and actionable.

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