Beyond Founder-Friendly: How Portfolio Size Shapes Investor Value (And Why I Changed My Mind)

๐Ÿ‘‹ Quick heads up: This newsletter challenges everything you think you know about portfolio management. Including what I thought I knew. 

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What you'll learn:

  • Why conventional wisdom about portfolio size and founder support is fundamentally flawed

  • A counterintuitive approach that turns large portfolios into an advantage

  • A practical 2-hour framework for delivering systematic value at any scale

Yeah, about that...

The Story: When Size Becomes Strength

Remember when I said large portfolios = worse founder support? Yeah, about that...

"Wholeheartedly disagree that this is the trade-off," Philipp Mรถhring, founder of Tiny VC, responded to that email. "You can have a small portfolio and be very aggressive vs founders, meddling and micro-managing, and you can have a large portfolio, focus on your strengths and trust the founder with other things."

Following up from that exchange, two hypotheses emerged from a lunch conversation last week:

  1. Most investors struggle to provide any real proactive value

  2. When they do invest time, the ROI is usually unclear

The Insight: Quality Over Quantity

The conventional formula is broken:

  • More portfolio companies โ‰  less value

  • Less attention โ‰  worse support

  • Portfolio size = potential leverage

Instead, focus on:

  1. Pick your superpower (one thing you're genuinely great at)

  2. Build a system to deliver it consistently

  3. Let your portfolio/community size amplify your impact

๐Ÿ› ๏ธ Want to implement this tomorrow? Here's your playbook:

The Quick Win: Your 2-Hour Value Engine

Step 1: Audit Your Value (30 mins)

  • List every founder interaction from last month

  • Circle the ones that actually moved the needle

  • Find the pattern (hint: it's not the "catch-up calls")

Step 2: Pick Your Lane (30 mins)

  • Choose ONE thing you do better than 90% of investors

  • Make it specific (not "hiring help" but "3 VP Engineering intros in 14 days")

  • Write down exactly how you'll deliver it

Step 3: Build Your System (1 hour)

  • Create a simple intake form

  • Set up your delivery workflow

  • Test with 3 portfolio companies

๐Ÿšซ What doesn't work:

  • Random "how can I help?" emails

  • Generic networking events

  • Being everyone's therapist

โœ… What does:

  • Specific, measurable support

  • Systems that scale

  • Focused expertise

The future of venture support isn't about time spent โ€“ it's about value delivered.

Want to dive deeper? Reply with "INVESTOR," and I'll send you my 25-page investor reflection guideโ€”hot off the press!

PS: Yes, of course, you are building a concentrated industry portfolio with deep knowledge in a specific industry, geo, or business model. Keep it going. You will still likely end up with 20+ portfolio companies in every fund. So the above applies to you, too.

Interested in more of my work?

If youโ€™ve made it this far, perhaps youโ€™d be interested in my other writing and resources:

1. Most read all time: Why I Stopped Using OKRs

3. New Cheat Sheets every month, full collection in this FOLDER. (16 in total, +4 since last time)

Want to work with me as a Coach & Catalyst for your business? Schedule a call HERE.

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